Amphidinolide B: Asymmetric synthesis of a C7-C20 synthon

Organic Letters

Volumn 8, Issue 1, 2006, Pages 7-10

  Gopalarathnam, Apsara ^a   Nelson, Scott G ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE D; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; STEREOISOMERISM;

EID: 30944464654     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051861l     Document Type: Article

References (36)

1. (a) Ishibashi, M.; Ohizumi, Y.; Hamashima, M.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J. J. Chem. Soc., Chem. Commun. 1987, 1127-1129.
2. (b) Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Yamasu, T.; Hirata, Y.; Sasaki, T.; Ohta, T.; Nozoe, S. J. Nat. Prod. 1989, 52, 1036-1042.
3. (c) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77-93.
4. Bauer, I.; Maranda, L.; Shimizu, Y.; Peterson, R. W.; Cornell, L.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 2657-2658.
5. (a) Chakraborty, T. K.; Thippeswamy, D.; Suresh, V. R. Chem. Lett. 1997, 563-564.
6. (b) Chakraborty, T. K.; Suresh, V. R. Chem. Lett. 1997, 565-566.
7. Lee, D. H.; Lee, S.-W. Tetrahedron Lett. 1997, 38, 7909-7910.
8. Cid, M. B.; Pattenden, G. Synlett 1998, 540-542.
9. (e) Ohi, K.; Shima, K.; Hamada, K.; Saito, Y.; Yamada, N.; Ohba, S.; Nishiyama, S. Bull. Chem. Soc. Jpn. 1998, 71, 2433-2440.
10. (f) Chakraborty, T. K.; Thippeswamy, D. Synlett 1999, 150-152.
11. (g) Ohi, K.; Nishiyama, S. Synlett 1999, 571-572.
12. (h) Ohi, K.; Nishiyama, S. Synlett 1999, 573-575.
13. (i) Ishiyama, H.; Takemura, T.; Tsuda, M.; Kobayashi, J. J. Chem. Soc., Perkin Trans. 1 1999, 1163-1166.
14. (j) Eng, H. M.; Myles, D. C. Tetrahedron Lett. 1999, 40, 2275-2278.
15. (k) Eng, H. M.; Myles, D. C. Tetrahedron Lett. 1999, 40, 2279-2282.
16. (l) Cid, B.; Pattenden, G. Tetrahedron Lett. 2000, 41, 7373-7378.
17. (m) Pattenden, G.; Sinclair, D. J. J. Organomet. Chem. 2002, 653, 261-268.
18. (n) Zhang, W.; Carter, R. G.; Yokochi, A. F. T. J. Org. Chem. 2004, 69, 2569-2572.
19. (o) Zhang, W.; Carter, R. G. Org. Lett. 2005, 7, 4209-4212.
20. Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruther, G. J. Am. Chem. Soc. 1997, 119, 698-708.
21. Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Perkin Trans. 1 1992, 2997-2998.
22. (a) Nelson, S. G.; Peelen, T. J.; Wan. Z. J. Am. Chem. Soc. 1999, 121, 9742-9743.
23. (b) Nelson, S. G.; Zhu, C.; Shen, X. J. Am. Chem. Soc. 2004, 126, 14-15.
24. This reaction was performed by Dr. Andrew J. Kassick. See: Kassick, A. J. Ph.D. Thesis, University of Pittsburgh, 2005.
25. (a) Lipshutz, B. H.; Sharma, S.; Reuter, D. C. Tetrahedron Lett. 1990, 31, 7253-7256.
26. (b) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938.
27. Regio- and stereoselectivity in the stannylcupration reaction was confirmed by NOE and DEPT analysis of iodide 3. See Supporting Information for full details of compound characterization
28. Nelson, S. G.; Wan, Z.; Stan, M. A. J. Org. Chem. 2002, 67, 4680-4683.
29. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
30. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979-982.
31. Takagi, J.; Takahashi, K.; Ishiyama. T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001-8006.
32. Wadsworth, W. S., Jr.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733-1738.
33. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
34. The absolute and relative stereochemistry of 21 was assigned on the basis of the Sharpless model for related allylic alcohol epoxidations but was not rigorously established by chemical correlation.
35. The boronic acid derivative of 22 proved to be a dramatically inferior coupling partner relative to the pinacolate boronic ester (33-50% conversion).
36. 2 may contribute to minimizing diene isomerization.