Home
Research
Gallery
The Group
Dirk Trauner
Members
Alumni
Publications
Teaching
denksport
resources
contact
news
↑ back to top

Denksport

Difficulty: 1 - 3, where 3 = most difficult
2023-03-08
Step count:
28
Difficulty:
3
Total Synthesis of Ginkgolide C and Formal Syntheses of Ginkgolides A and B

Hébert, M.; Bellavance, G.; Barriault, L. J. Am. Chem. Soc. 2022, 144, 17792-17796.

2023-02-22
Step count:
17
Difficulty:
2
Total Synthesis of (-)-Daphenylline

Xu, B.; Wang, B.; Xun, W.; Qiu, F. G. Angew. Chem. Int. Ed. 2019, 58, 5754–5757.

2023-02-15
Step count:
31
Difficulty:
3
Total Synthesis of Yuzurine-type Alkaloid Daphgraciline

Li, L.-X.; Min, L.; Yao, T.-B.; Ji, S.-X.; Qiao, C.; Tian, P.-L.; Sun, J.; Li, C.-C. J. Am. Chem. Soc. 2022, 144, 18823–18828.

2023-02-09
Step count:
32
Difficulty:
3
Total Synthesis of Puberuline C

Shimakawa, T.; Nakamura, S.; Asai, H.; Hagiwara, K.; Inoue, M. J. Am. Chem. Soc. 2023, 145, 600–609.

2023-01-26
Step count:
11
Difficulty:
2
Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G

Hu, L.; Rawal, V. H. J. Am. Chem. Soc. 2021, 143, 10872–10875.

2022-12-08
Step count:
21
Difficulty:
1
Enantioselective Total Synthesis of (+)-Tricycloclavulone

Ito,H.;* Hasegawa, M.; Takenaka, Y.; Kobayashi, T.; Iguchi, K.* J. Am. Chem. Soc. 2004, 126, 4520–4521.

2022-11-22
Step count:
16
Difficulty:
1
Asymmetric Total Syntheses of Hypoestin A, Albolic Acid, and Ceroplastol II

Wang, Y.; Xu, K.; Min, L.; Li, C. J. Am. Chem. Soc. 2022, 144, 10162–10167.

2022-11-10
Step count:
14
Difficulty:
1
Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Miloserdov, F. M.; Kirillova, M. S.; Muratore, M. E.; Echavarren, A. M. J. Am. Chem. Soc. 2018, 140, 5393–5400.

2022-11-03
Step count:
20
Difficulty:
2
Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (–)-Longirabdolactone, and (–)-Effusin

Zhang, J.;Li, Z.; Zhuo, J.; Cui, Y.; Han, T.; Li, C. J. Am. Chem. Soc. 2019, 141, 8372–8380.

2022-10-27
Step count:
14
Difficulty:
1
14-Step Synthesis of (+)-Ingenol from (+)-3-Carene

Jørgensen, L.; McKerrall, S. J.; Kuttruff, C. A.; Ungeheuer, F.; Felding, J.; Baran, P. S. Science, 2013, 341, 878–882

2022-10-20
Step count:
29
Difficulty:
3
Asymmetric Total Synthesis of Hispidanin A

Deng, H.; Cao, W.; Liu, R.; Zhang, Y.; Liu, B. Angew. Chem. Int. Ed. 2017, 56, 5849–5852.

2022-10-13
Step count:
23
Difficulty:
2
Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy

Truax, N. J.;  Ayinde, S.; Liu, J. O.; Romo, D. J. Am. Chem. Soc. 2022, 144, 18575-18585

2022-09-22
Step count:
28
Difficulty:
3
Enantioselective Total Synthesis of Cotylenin A

Uwamori, M.; Osada, R.; Sugiyama, R.; Nagatani, K.; Nakada, M. J. Am. Chem. Soc. 2020, 142, 5556–5561.

2022-09-08
Step count:
25
Difficulty:
2
Synthesis of (+)-CP-263,114

Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 7424-7425.

2022-09-01
Step count:
22
Difficulty:
2
Enantioselective Total Synthesis of (+)-Euphorikanin A

Classen, M. J.; Böcker, M. N. A.; Roth, R.; Amberg, W. M.; Carreira, E. M. J. Am. Chem. Soc. 2021, 143, 8261–8265.

2022-08-25
Step count:
24
Difficulty:
3
Total Syntheses of (–)-Acutumine and (–)-Dechloroacutumine

King, S. M.; Calandra, N. A.; Herzon, S. B. Angew. Chem. Int. Ed. 2013, 52, 3642–3645.

2022-08-18
Step count:
13
Difficulty:
3
Total Synthesis of (+)-6-epi-Ophiobolin A

Thach, D. Q.; Brill, Z. G.; Grover, H. K.; Esguerra, K. V.; Thompson, J. K.; Maimone, T. J. Angew. Chem. Int. Ed. 2020, 59, 1532–1536.

2022-08-11
Step count:
17
Difficulty:
3
Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach

Yu, K.; Yao, F.; Zeng, Q.; Xie, H.; Ding, H. J. Am. Chem. Soc. 2010, 132, 8506–8512

2022-07-25
Step count:
16
Difficulty:
1
Transition-Metal-Mediated Chemo- and Stereoselective Total Synthesis of (−)-Galanthamine

Miller, I. R.; McLean, N. J.; Moustafa, G. A. I.; Ajavakom, V.; Kemp, S. C.; Bellingham, R. K.; Camp, N. P.; Brown, R. C. D. J. Org. Chem. 2022, 87, 1325-1334

2022-07-18
Step count:
14
Difficulty:
1
Total Synthesis of (+)-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2+2] Cycloaddition

Richardson, A. D.; Trenton, R. V; Traficante, E. F.; Glover, K. J.; Schindler, C. S. Angew. Chem. Int. Ed. 2022, e202201213.

2022-07-11
Step count:
13
Difficulty:
2
Total Syntheses of (+)-Aquatolide and Related Humulanolides

Takao, K.-I.; Kai, H.; Yamada, A.; Fukushima, Y.; Komatsu, D.; Ogura, A.; Yoshida, K. Angew. Chem. Int. Ed. 2019, 58, 9851–9855.

2022-06-27
Step count:
19
Difficulty:
2
Total Synthesis of Daphenylline, Daphnipaxianine A, and Himalenine D

Chen, Y.; Zhang, W.; Ren, L.; Li, J.; Li, A. Angew. Chem. Int. 2018, 130, 964–968.

2022-06-13
Step count:
16
Difficulty:
1
A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K

Michalak, S. E.; Nam, S.; Kown, D. M.; Horne, D. A.; Vanderwal, C. D, J. Am. Chem. Soc. 2019, 141, 9202–9206

2022-06-06
Step count:
18
Difficulty:
1
Asymmetric Total Synthesis of (+)-Mannolide C

Ao, Q.; Zhang, H-J.; Zheng, J.; Chen, X.; Zhai, H. Angew. Chem. Int. Ed. 2021, 60, 21267-21271

2022-05-30
Step count:
16
Difficulty:
1
Total Synthesis of (±)-Isophellibiline

Funk, R. L.; Belmar, J. Tetrahedron Lett. 2012, 53, 176–178.

2022-05-16
Step count:
17
Difficulty:
2
Asymmetric Total Synthesis of (2R)‑Hydroxynorneomajucin, a Norsesquiterpene from Illicium jiadifengpi

Dooley, C.; Rychnovsky, S. Org. Lett. 2022, 24, 3411–3415.

2022-05-09
Step count:
14
Difficulty:
1
Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A

Hou, S.-H.; Prichina, A. Y.; Dong, G. Angew. Chem. Int. Ed. 2021, 60, 13057–13064.

2022-05-02
Step count:
14
Difficulty:
1
Asymmetric Total Synthesis of Laurallene

Yoshimura, F.; Okada, T.; Tanino, K. Org. Lett. 2019, 21, 559-562

2022-04-25
Step count:
12
Difficulty:
1
β-Ketoesters as Mono- or Bisnucleophiles: A concise Enantioselective Total synthesis of (-)-Englerin A and B

Guo, L.; Plietker, B. Angew. Chem. Int. Ed. 2019, 58, 8346-8350.

2022-04-18
Step count:
17
Difficulty:
2
Total Synthesis of (±)-Perophoramide

Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068-5069.

2022-04-11
Step count:
20
Difficulty:
2
The Total Synthesis of (±)-11-O-Debenzoyltashironin

Cook, S. P.; Polara, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 16440–16441.

2022-04-04
Step count:
25
Difficulty:
2
Total Synthesis of Vinigrol

T. J. Maimone, J. Shi, S. Ashida, P. S. Baran, J. Am. Chem. Soc. 2009, 131, 17066-17067.

2022-03-28
Step count:
31
Difficulty:
3
Total Synthesis of Gukulenin B via Sequential Tropolone Functionalizations

Nicolaou, K. C.; Yu, R.; Lu, Z.; Alvarez, F. G. J. Am. Chem. Soc. 2022, 144, 5190–5196

2022-03-21
Step count:
21
Difficulty:
2
Synthesis of Swinhoeisterol A, Dankasterone A and B, and Periconiastone A by Radical Framework Reconstruction

Duecker, F. L.; Heinze, R. C.; Heretsch, H. J. Am. Chem. Soc. 2020, 142, 104-108.

2022-03-14
Step count:
34
Difficulty:
3
Asymmetric Total Synthesis of Norzoanthamine

Xin, Z.; Wang, H.; He, H.; Zhao, X.; Gao, S. Angew. Chem. Int. Ed. 2021, 60, 12807-12812.

2022-03-07
Step count:
29
Difficulty:
3
Bidirectional Total Synthesis of Phainanoid A via Strategic Use of Ketones

Xie, J.; Liu, X.; Zhang, N.; Choi S.; Dong, G. J. Am. Chem. Soc. 2021, 143, 19311–19316.

2022-02-28
Step count:
28
Difficulty:
2
Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene

Guo, L.-D.; Xu, Z.; Tong, R. Angew. Chem. Int. Ed. 2022, 61, e202115384.

2022-02-21
Step count:
24
Difficulty:
3
Total Synthesis of (−)-Rhodomollanol A

Gao, J.; Rao, P.; Xu, K.; Wang, S.; Wu, Y.; He, C.; Ding, H. J. Am. Chem. Soc. 2020, 142, 4592-4597.

2022-02-14
Step count:
23
Difficulty:
1
Total Synthesis of (±)-Leonuketal

Grant, P. S.; Furkert, D. P.; Brimble, M. A. Org. Lett. 2020, 22, 8735-8740.

2022-02-07
Step count:
18
Difficulty:
3
Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A

Wang, X.; Wang, Z.; Ma, X.; Huang, Z.; Sun, K.; Gao, X.; Fu, S.; Liu, B. Angew. Chem. Int. Ed. 2022, ASAP.

2022-01-31
Step count:
14
Difficulty:
2
Total Synthesis of (of (−)-Daphnezomines A and B

Xu, G.; Wu, J.; Li, L.; Lu, Y.; Li, C. J. Am. Chem. Soc. 2020, 142, 15240-15245.

2022-01-24
Step count:
15
Difficulty:
2
A Short Synthesis of Delavatine A Unveils New Insights into Site-Selective Cross-Coupling of 3,5-Dibromo-2-pyrone

Palani, V.; Hugelshofer, C. L.; Kevlishvili, L.; Liu, P.; Sarpong, R. J. Am. Chem. Soc. 2019, 141, 2652−2660.

2022-01-17
Step count:
15
Difficulty:
1
A biomimetic total synthesis of (+)-intricarene

Tang, B.; Bray, C. D.; Pattenden G. Tetrahedron Lett. 2006, 47, 6401–6404.

2022-01-10
Step count:
15
Difficulty:
1
Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach

Douki, K.; Ono, H.; Taniguchi, T.; Shimokawa, J.; Kitamura, M.; Fukuyama, T. J. Am. Chem. Soc. 2016, 138, 14578−14581

2021-12-20
Step count:
13
Difficulty:
2
Ir-Catalyzed Asymmetric Total Syntheses of Bisdehydrotuberostemonine D, Putative Bisdehydrotuberostemonine E and Structural Revision of the Latter

Deng, Y.; Liang, X.; Wei, K.; Yang, Y. R. J. Am. Chem. Soc. 2021, 143, 20622–20627

2021-12-13
Step count:
15
Difficulty:
1
Total Synthesis of Nesteretal A

Kawamoto, Y.; Kitsukawa, H.; Kobayashi, T.; Ito, H. Org. Lett. 2021, 23, 7074–7078.

2021-12-06
Step count:
15
Difficulty:
1
Stereoselective Synthesis of (±)-Cephanolide B

Li, A.; He, Z.; Liu, B.; Yang, Z.; Zhang, Z. Org. Lett. 2021, 23, 9237-9240.

2021-11-29
Step count:
12
Difficulty:
1
Asymmetric Total Syntheses of Schizozygane Alkaloids

Zhou, W.; Zhou, T.; Tian, M.; Jiang, Y.; Yang, J.; Lei, S.; Wang, Q.; Zhang, C.; Qiu, H.; He, L.; Wang, Z. J. Am. Chem. Soc. 2021, 143, 19975–19982.

2021-11-22
Step count:
17
Difficulty:
2
Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid

Walker, J. R.; Merit, J. E.; Thomas-Tran, R.; Tang, D. T. Y.; DuBois, J.  Angew. Chem. Int. Ed. 2019, 58, 1689–1693.

2021-11-15
Step count:
24
Difficulty:
3
Asymmetric Total Synthesis of Pre-schisanartanin C

Jiang, Y.-L.; Yu, H.-X.; Li, Y.; Q, P.; Han, Y.-X.; Chen, J.-H.*; Yang, Z.* J. Am. Chem. Soc. 2020, 142, 573– 580.

2021-11-01
Step count:
10
Difficulty:
1
An Efficient, Stereocontrolled, Total Synthesis of the Orchidaceae Alkaloid (±)-Dendrobine

Lee, C. H.; Westling, M.; Livinghouse, T.: Williams, A. C. J. Am. Chem. Soc. 1992, 114, 4089–4095

2021-10-25
Step count:
26
Difficulty:
3
Total Synthesis and Structural Revision of a Harziane Diterpenoid

Hönig, M; Carreira, E. M. Angew. Chem. Int. Ed. 2020, 59, 1192–1196

2021-10-18
Step count:
18
Difficulty:
1
Concise Total Synthesis of Peyssonnoside A

Chesnokov, G. A.; Gademann, K. J. Am. Chem. Soc. 2021, 143, 14083-14088

2021-10-04
Step count:
45
Difficulty:
2
Total Synthesis of Limaol

S. N. Hess, X. Mo, C. Wirtz, and A. Fürstner. J. Am. Chem. Soc. 2021, 143, 6, 2464–2469.

2021-09-27
Step count:
25
Difficulty:
2
Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (−)-Jiadifenin

X. Cheng, G. C. Micalizio, J. Am. Chem. Soc. 2016, 138, 1150-1153

2021-09-20
Step count:
12
Difficulty:
1
Enantioselective Total synthesis of (+)-Garsubellin A

Jang, D.; Choi, M.; Chen, J. D.; Lee, C. Angew. Chem. Int. Ed. 2021, 60, 1 – 6

2021-08-30
Step count:
29
Difficulty:
3
Total Syntheses of the C19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach

Wong, A. R.; Fastuca, N. J.; Mak, V. W.; Kerkovius, J. K.; Stevenson, S. M.; Reisman, S. E. ACS Cent. Sci. 2021, 7, 1311–1316

2021-08-23
Step count:
25
Difficulty:
3
Asymmetric Total Synthesis of (−)-Spirochensilide A

Liang, X-T.; Chen, J-H.; Yang, Z. J. Am. Chem. Soc. 2020, 142, 8116–8121.

2021-08-16
Step count:
19
Difficulty:
2
Concise and Stereoselective Synthesis of Annotinolides C, D, and E

Qu, P.; Snyder, S. J. Am. Chem. Soc. 2021, 143, 11951–11956.

2021-08-09
Step count:
7
Difficulty:
2
Synthesis of Brevianamide A and B

Godfrey, R. C.; Green, N. J.; Nichol, G. S.; Lawrence, A. L. Nat. Chem. 2020, 12, 615-619.

2021-08-02
Step count:
19
Difficulty:
3
Total Synthesis of Epicolactone

Kravina, A. G.; Carreira, E. M. Angew. Chem. Int. Ed. 2018, 57, 13159–13162.

2021-07-26
Step count:
37
Difficulty:
2
Total Synthesis of Putative Chagosensine

Heinrich, M.; Murphy, J. J.; Ilg, M. K.; Letort, A.; Frasz, J.; Philipps, P.; Fürstner, A. Angew. Chem. Int. Ed. 2017, 57, 13578–13581.

2021-07-19
Step count:
19
Difficulty:
3
Total Synthesis of (–)-Tubingensin B Enabled by the Strategic Use of an Aryne Cyclization

Corsello, M. A.; Kim, J.; Garg, N. K. Nat. Chem. 2017, 9, 944–949

2021-07-12
Step count:
16
Difficulty:
1
Tandem C–H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (–)-brussonol and (–)-przewalskine E

Jiao Z.; Tu Y.; Zhang Q.; Liu W.; Zhang S.; Wang S.; Zhang F.; Jiang S. E. Nat. Commun. 2015, 6, 7332.

2021-06-28
Step count:
12
Difficulty:
1
Enantioselective Total Synthesis and Structural Revision of Dysiherbol A

Baars, J.; Grimm, I.; Blunk, D.; Neudörfl, J.-M; Schmalz, H.-G Angew. Chem. Int. Ed. 2021, 60, 14915–14920.

2021-06-21
Step count:
13
Difficulty:
2
Asymmetric Total Synthesis and Biosynthetic Implications of Perovskones, Hydrangenone, and Hydrangenone B

Yang, B.; Wen G.; Zhang Q.; Hou, M.; He. H.; Gao, S. J. Am. Chem. Soc. 2021, 143, 6370–6375

2021-06-14
Step count:
12
Difficulty:
2
Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

Anthony, S. M.; Tona, V.; Zou, Y.; Morrill, L. A.; Billingsley, J. M.; Lim, M.; Tang, Y.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2021, 143, 7471–7479.

2021-06-07
Step count:
19
Difficulty:
2
Enantioselective Total Synthesis of (+)-Euphorikanin A

Classen, M. J.; Böcker, M. N. A.; Roth, R.; Amberg, W. M.; Carreira, E. M. J. Am. Chem. Soc. 2021, 143, 8261-8265

2021-06-01
Step count:
12
Difficulty:
3
Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

Zhang, Y.; Xue, Y.; Li, G.; Yuan, H.; Luo, T. Chem. Sci. 2016, 7, 5530–5536

2021-05-24
Step count:
22
Difficulty:
1
Total Synthesis of the Meroterpenoid Manginoid A as Fueled by a Challenging Pinacol Coupling and Bicycle-forming Etherification

Zhang, T.; Milkovits, A.; Agarawal, V.; Taylor, C. A.; Snyder, S. A. Angew. Chem. Int. Ed. 2021, 60, 11127-11132.

2021-05-17
Step count:
23
Difficulty:
1
Clinical Targeting of HIV Capsid Protein With a Long-Acting Small Molecule

Link, J. O.; Rhee, M. S.; Tse, W. C. et al. Nature 2020, 584, 614–618.

2021-05-10
Step count:
25
Difficulty:
2
Asymmetric Total Synthesis of Dankasterones A and B and Periconiastone A Through Radical Cyclization

Chen, P.; Wang, C.; Yang, R.; Xu, H.; Wu, J.; Jiang, H.; Chen, K.; Ma, Z. Angew. Chem. Int. Ed. 2021, 60, 5512– 5518

2021-05-03
Step count:
17
Difficulty:
2
Efficient Method for the Synthesis of Amino-1,3-Oxazines from Thioureas

Richardson, J.*; Lindsay-Scott, P. J.; Larichev, V.; Pocock, E. Org. Process Res. Dev. 2020, 24, 2853−2863.

2021-04-26
Step count:
19
Difficulty:
1
Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction

Reuß, F.; Heretsch, P. Org. Lett. 2020, 22, 3956–3959.

2021-04-19
Step count:
20
Difficulty:
1
Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo-[3.3.0]octanone Fragment

Allred, T. K.;  Dieskau, A. P.; Zhao, P.;  Lackner, G. L.;  Overman, L. E. Angew. Chem. Int. Ed. 2020, 59, 6268–6272.

2021-04-12
Step count:
25
Difficulty:
1
Total Synthesis of (+)-Vallesamidine and (+)-14,15-Dehydrostrempeliopine

X. Zhang, J. C. Anderson. Angew. Chem. Int. Ed. 2019, 58, 18040−18045.

2021-04-05
Step count:
18
Difficulty:
1
Total Synthesis of (–)-Jiadifenin

Yang, Y.; Fu, X.; Chen, J.; Zhai, H. Angew. Chem. Int. Ed. 2012, 51, 9825–9828

2021-03-29
Step count:
13
Difficulty:
2
Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A

Ting, C.; Xu, G.; Zeng, X.; Maimone, T. J. Am. Chem. Soc. 2016, 138, 14868−14871

Xu, G.; Elkin, M.; Tantillo, D. J.; Newhouse, T. R.; Maimone, T. J. Angew. Chem., Int. Ed. 2017, 56, 12498−12502 [link]

2021-03-22
Step count:
23
Difficulty:
1
Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis

Donohoe*, T. J.;  Jones, C. R.; Barbosa, L. C. A. J. A. Chem. Soc. 2011, 133, 16418–16421.

2021-03-15
Step count:
23
Difficulty:
1
Total Synthesis of the Marine Diterpenoid Blumiolide C

Hamel, C.; Prusov, E. V.; Gertsch, J.; Schweizer, W. B.; Altmann, K-H. Angew. Chem. Int. Ed. 2008, 47, 10081–10085

2021-03-08
Step count:
19
Difficulty:
2
Total Synthesis of (±)-11-O-Debenzoyltashironin via Palladium-Catalyzed 5-endo Ene-yne Cyclization Enabled trans-5–6 Ring Fusion

Tong, J.; Xia, T.; Wang, B. Org. Lett. 2020, 22, 7, 2730–2734

2021-03-01
Step count:
26
Difficulty:
2
Synthesis of Leucascandrolide A via a Spontaneous Macrolactolization

Wang, Y.; Janjic, J.; Kozmin, S. J. Am, Chem. Soc. 2002, 124, 13670–13671. [link]

Kozmin, S. Org. Lett. 2001, 3, 755–758. [link]

2021-02-22
Step count:
24
Difficulty:
2
Total Synthesis and Stereochemical Reassignment of (±)-Indoxamycin B

Jeker, O. F.; Carreira, E. M. Angew. Chem. Int. Ed. 2012, 51, 3474-3477.

2021-02-08
Step count:
14
Difficulty:
1
Total Synthesis of the Diterpene Waihoensene

Rosenbaum, L.-C.; Häfner, M.; Gaich, T. Angew. Chem. Int. Ed. 2021, 60, 2939-2942.

2021-02-01
Step count:
19
Difficulty:
2
Synthesis of (–)-Fumagillin

Taber, D. F.*; Christos, T. E.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1999, 121, 5589-5590.

2021-01-25
Step count:
15
Difficulty:
2
Mimicking Oxidative Radical Cyclization of Lignan Biosynthesis using Redox-Neutral Photocatalysis

Zheng, H; Lumb, J. P. Nat. Chem. 2021, 13, 24-32.

2021-01-18
Step count:
12
Difficulty:
1
Protecting-Group-Free Syntheses of ent-Kaurane Diterpenoids: [3+2+1] Cycloaddition/Cycloalkenylation Approach

Wang, J.; Hong, B.; Hu D.-C.; Kadonaga, Y.; Tang, R.-Y.; Lei, X.-G. J. Am. Chem. Soc. 2020, 142, 2238–2243.

2021-01-11
Step count:
8
Difficulty:
1
Discovery of NVP-BYL719 a Potent and Selective Phosphatidylinositol-3 kinase Alpha Inhibitor Selected for Clinical Evaluation

Furet, P.; Guagnano, V.; Fairhurst, R. A.; Imbach-Weese, P.; Bruce, I.; Knapp, M.; Fritsch, C.; Blasco, F.; Blanz, J.; Aichholz, R.; Hamon, J.; Fabbro, D.; Caravatti, G. Bioorg. Med. Chem. Lett. 2013, 23, 3741–3748.

2020-12-21
Step count:
25
Difficulty:
2
Total Synthesis of (−)-Crinipellin A

Kang, T.; Song, S. B.; Kim, W.; Kim, B. G.; Lee, H. J. Am. Chem. Soc. 2014, 136, 10274–10276

2020-12-14
Step count:
19
Difficulty:
1
Synthesis of Eupalinilide E, a Promoter of Human Hematopoietic Stem and Progenitor Cell Expansion

T. C. Johnson, M. R. Chin, T. Han, J. P. Shen, T. Rana, D. Siegel.  J. Am. Chem. Soc. 2016, 138, 6068−6073

2020-12-07
Step count:
22
Difficulty:
2
Total Synthesis of (−)-Himalensine A

Shi, H.; Michaelides, I. N.; Darses, B.; Jakubec, P.; Nguyen, Q. N. N.; Paton, R. S.; Dixon, D. J. J. Am. Chem. Soc. 2017, 139, 17755–17758.

2020-11-30
Step count:
24
Difficulty:
1
Total Synthesis of (+)-Haperforin G

Zhang, W.; Zhang, Z.; Tang, J.-C.; Che, J.-T.; Zhang, H.-Y.; Chen, J.-H.; Yang, Z. J. Am. Chem. Soc. 2020, 142, 19487–19492

2020-11-23
Step count:
31
Difficulty:
1
Total Synthesis of Liangshanone

Huang, H.-X.; Mi, F.; Li, C.; He, H.; Wang, F.-P.; Liu, X.-Y.; Qin, Y. Angew. Chem. Int. Ed. 2020, 59, 1-7.

2020-11-16
Step count:
29
Difficulty:
2
Scalable Synthesis of Bryostatin 1 and Analogs, Adjuvant Leads Against Latent HIV

Wender, P. A.; Hardman, C. T.; Ho, S.; Jeffreys, M. S.; Maclaren, J. K.; Quiroz, R. V.; Ryckbosch S. M.; Shimizu, A. J.; Sloane, J. L.; Stevens, M. C. Science, 2017, 358, 218-223.

2020-11-09
Step count:
23
Difficulty:
1
Enantioselective Total Synthesis of the Diterpenes Kempene‐2, Kempene‐1, and 3‐epi‐Kempene‐1 from the Defense Secretion of Higher Termites

Schubert, M.; Metz, P. Angew. Chem. Int. Ed. 2011, 50, 2954–2956.

2020-11-02
Step count:
24
Difficulty:
2
Synthesis of Streptolydigin, a Potent Bacterial RNA Polymerase Inhibitor

Pronin, S. V.; Kozmin, S. A. J. Am. Chem. Soc. 2010, 132, 14394−14396.

2020-10-26
Step count:
15
Difficulty:
2
Total Synthesis of Tagetitoxin

He, C.; Chu, H.; Stratton, T. P.; Kossler, D.; Eberle, K. J.; Flood, D. T.; Baran, P. S. J. Am. Chem. Soc. 2020, 142, 13683–13688.

2020-10-19
Step count:
24
Difficulty:
2
Asymmetric Total Synthesis of Cyclocitrinol

Liu, J.; Wu, J.; Fan, J.-H.; Yan, X.; Mei, G.; Li, C.-C.; J. Am. Chem. Soc. 2018, 140, 5365–5369.

2020-10-12
Step count:
15
Difficulty:
1
Total Synthesis of (–)-Nakadomarin A

Bonazzi, S.; Cheng, B.; Wzorek, J. S.; Evans, D. A. J. Am. Chem. Soc. 2013, 135, 9338–9341.

2020-09-28
Step count:
12
Difficulty:
1
Total Synthesis of (±)-Chloranthalactone A

Yue, G.; Yang, L.; Yuan, C.; Jiang, X.; Liu, B.; Org. Lett. 2011, 13, 5460–5408.