Stereoselective total synthesis of the pseudopterolide kallolide A

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5962-5970

  Marshall, James A ^a   Liao, Junkai ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KALLOLIDE A; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOMER; ISOMERISM; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032555401     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980603h     Document Type: Article

References (27)

1. Bandurraga, M. M.; Fenical, W.; Donovan, S. F.; Clardy, J. J. Am. Chem. Soc. 1982, 104, 6463.
2. Look, S. A.; Burch, M. T.; Fenical, W.; Zhen, Q.-t.; Clardy, J. J. Org. Chem. 1985, 50, 5741.
3. Marshall, J. A.; Bartley, G. S.; Wallace, E. M. J. Org. Chem. 1996, 61, 5729.
4. For a review of synthetic efforts in this area see Marshall, J. A. Recent Res. Devel. Org. Chem. 1997, 1, 1.
5. Marshall, J. A. Chem. Rev. 1996, 96, 31.
6. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
7. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Ireland, R. E.; Lin, L. J. Org. Chem. 1993, 58, 2899.
8. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Ireland, R. E.; Lin, L. J. Org. Chem. 1993, 58, 2899.
9. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
10. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
11. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
12. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920. Marshall, J. A. Chemtracts-Org. Chem. 1997, 10, 481.
13. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920. Marshall, J. A. Chemtracts-Org. Chem. 1997, 10, 481.
14. Weigand, S.; Brückner, R. Synthesis 1996, 475.
15. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620. Kobayashi, S.; Yasuda, M.; Nishio, K. Synlett 1996, 153.
16. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620. Kobayashi, S.; Yasuda, M.; Nishio, K. Synlett 1996, 153.
17. Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
18. Hyde, E. G.; Thornhill, S. M.; Boyer, A. J.; Abrahamson, S. N. J. Med. Chem. 1995, 38, 4704.
19. The program Macromodel V5.5 was employed for these calculations. Global minimum multiple conformer searching was achieved with the Monte Carlo subroutine in BATCHMIN through multiple step interations (typically 1000) until the minimum energy conformer was found multiple times (10 or more). For a description of the program, see: (a) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. (b) Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
20. The program Macromodel V5.5 was employed for these calculations. Global minimum multiple conformer searching was achieved with the Monte Carlo subroutine in BATCHMIN through multiple step interations (typically 1000) until the minimum energy conformer was found multiple times (10 or more). For a description of the program, see: (a) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. (b) Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
21. The structure determination was performed by Dr. Michal Sabat of this department.
22. Wu, Y. D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421.
23. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827.
24. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827.
25. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561. Marshall, J. A.; Tang, Y. Synlett 1992, 653.
26. Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561. Marshall, J. A.; Tang, Y. Synlett 1992, 653.
27. The furanocembrane bipinnatin J has recently been converted to kallolide A through photochemical ring contraction. Rodriguez, A.; Shi, J.-G.; J. Org. Chem. 1998, 63, 420.