Fragmentation enables complexity in the first total synthesis of vinigrol

Angewandte Chemie - International Edition

Volumn 49, Issue 13, 2010, Pages 2286-2288

  Lu, Jin Yong ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Diterpenes; Natural products; Total synthesis; Vinigrol

Indexed keywords

CHEMICAL ENGINEERING; CHEMICAL REACTIONS; CHEMISTRY;

DITERPENES; FUNCTIONALIZATION REACTIONS; INTRAMOLECULAR DIELS-ALDER REACTION; NATURAL PRODUCTS; STEREOGENIC CENTERS; TOTAL SYNTHESIS; TRICYCLIC FRAMEWORKS; VINIGROL;

SYNTHESIS (CHEMICAL);

ANTIHYPERTENSIVE AGENT; DITERPENE; VINIGROL;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; NOTE; SYNTHESIS;

ANTIHYPERTENSIVE AGENTS; CYCLIZATION; DITERPENES; MOLECULAR STRUCTURE;

EID: 77953499110     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906826     Document Type: Article

References (19)

1. For a review, see: G. Tessier, L. Barriault, Org. Prep. Proced. Int. 2007, 39, 311-353.
2. a) I. Uchida, T. Ando, N. Fukami, K. Yoshida, M. Hashimoto, T. Tada, S. Koda, Y. Morimoto, J. Org. Chem. 1987, 52, 5292-5293;
3. b) T. Ando, Y. Tsurumi, N. Ohata, I. Uchida, K. Yoshida, M. Okuhara, J. Antibiot. 1988, 41, 25-30;
4. c) T. Ando, K. Yoshida, M. Okuhara, J. Antibiot. 1988, 41, 31-35.
5. S. N. Goodman, PhD Thesis, Harvard University, 2000.
6. C. M. Grisé, G. Tessier, L. Barriault, Org. Lett. 2007, 9, 1545-1548.
7. M. S. Souweha, G. D. Enright, A. G. Fallis, Org. Lett. 2007, 9, 5163-5166.
8. a) L. A. Paquette, R. Guevel, S. Sakamoto, I. H. Kim, J. Crawford, J. Org. Chem. 2003, 68, 6096-6107;
9. b) L. A. Paquette, I. Efremov, Z. Liu, J. Org. Chem. 2005, 70, 505-509;
10. c) L. A. Paquette, I. Efremov, J. Org. Chem. 2005, 70, 510-513.
11. M. Kito, T. Sakai, H. Shirahama, M. Miyashita, F. Matsuda, Synlett 1997, 219-220.
12. a) J.-F. Devaux, I. Hanna, J.-Y. Lallemand, J. Org. Chem. 1993, 58, 2349-2350;
13. b) L. Gentric, I. Hanna, L. Ricard, Org. Lett. 2003, 5, 1139-1142;
14. c) L. Gentric, X. L. Goff, L. Ricard, I. Hanna, J. Org. Chem. 2009, 74, 9337-9344.
15. J. G. M. Morton, C. Draghici, L. D. Kwon, J. T. Njardarson, Org. Lett. 2009, 11, 4492-4495.
16. a) T. J. Maimone, A.-F. Voica, P. S. Baran, Angew. Chem. 2008, 120, 3097-3099;
17. Angew. Chem. Int. Ed. 2008, 47, 3054-3056;
18. b) T. J. Maimone, J. Shi, S. Ashida, P. S. Baran, J. Am. Chem. Soc. 2009, 131, 17066-17067;
19. c) T. J. Maimone, PhD Thesis, The Scripps Research Institute, 2009.