Alkene-alkyne coupling as a linchpin: An efficient and convergent synthesis of amphidinolide P

Journal of the American Chemical Society

Volumn 126, Issue 42, 2004, Pages 13618-13619

  Trost, Barry M ^a   Papillon, Julien P N ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMPHIDINOLIDE P; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DEPROTECTION REACTION; DIASTEREOISOMER; LACTONIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SEPARATION TECHNIQUE; STOICHIOMETRY; SYNTHESIS;

ALKENES; ALKYNES; HETEROCYCLIC COMPOUNDS; MACROLIDES;

EID: 6444234181     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045449x     Document Type: Article

References (30)

1. Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
2. (a) Trost, B. M.; Shen, H. C.; Pinkerton, A. B. Chem. - Eur. J. 2002, 8, 2341.
3. (b) Trost, B. M.; Machacek, M.; Schanderbeck, M. J. Org. Lett. 2000, 2, 1761.
4. (c) Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
5. (d) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
6. (a) Trost, B. M.; Harrington, P. E. J. Am. Chem. Soc. 2004, 126, 5028.
7. (b) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
8. Ishibashi, M.; Takahashi, J.; Kobayashi, J. J. Org. Chem. 1995, 60, 6062.
9. Williams, D. R.; Myers, B. J.; Mi, L. Org. Lett. 2000, 2, 945.
10. Skrydstrup, T.; Bénéchie, M.; Khuong-Huu, F. Tetrahedron Lett. 1990, 31, 7145.
11. Ishiara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490.
12. Mikami, K.; Kawamoto, K.; Loh, T. P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1161.
13. NOE studies of the tetrahydofuran derived from 13 gave a 5.0% NOE between H-4 and H-6, thereby further supporting the assignment of the stereochemistry of the 4,5-syn chelation-controlled product 12 as 5,6-anti. (Chemical Equation Presented)
14. (a) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
15. (b) Ohira, S. Synth. Commun. 1989, 19, 561.
16. Nicolaou, K. C.; Li, Y.; Fylaktadikou, K. C.; Mitchell, H. J.; Wei, H.-X.; Weyershausen, B. Angew. Chem., Int. Ed 2001, 40, 3849.
17. (a) Lipshutz, B. H.; Kozlowski, J. A.; Parker, D. A.; Nguyen, S. L.; McCarthy, K. E. J. Organomet Chem. 1985, 285, 437.
18. (b) Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, U.K., 1994.
19. Klunder, J. M.; Onami, T.; Sharpless, K. B. J. Org. Chem. 1989, 54, 1295.
20. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. L.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
21. Higashibayashi, S.; Shinko, K.; Ishizu, T.; Hashimoto, K.; Shirahama, H.; Nakata, M. Synlett 2000, 1306.
22. (a) Zaitseva, G. S.; Vinokurova, N. G.; Baukov, Y. I. Zh. Obshch. Khim. 1975, 45, 1398.
23. (b) Concepcion, A. B.; Maruoka, K.; Yamamoto, H. Tetrahedron 1995, 51, 4011.
24. Ruden, R. A. J. Org. Chem. 1974, 39, 3607.
25. Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464.
26. (a) Otera, J.; Ioka, S.; Nozaki, H. J. Org. Chem. 1989, 54, 4013.
27. (b) Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
28. (c) Orita, A.; Sakamoto, K.; Hamada, Y.; Mitsutome, A.; Otera, J. Tetrahedron 1999, 55, 2899.
29. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
30. 5 The source of this discrepancy is unclear.