Total synthesis of the pseudopterane (-)-kallolide B, the enantiomer of natural (+)-kallolide B

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5729-5735

  Marshall, James A ^a   Bartley, Gary S ^a   Wallace, Eli M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; KALLOLIDE B; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029829408     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960798y     Document Type: Article

References (36)

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5. Aldrich Chemical Co., Milwaukee, WI. The 1995 catalogue lists the (R) enantiomer at $26.00/g and the (S) enantiomer at $2.12/g.
6. This sequence was first performed by Clark Sehon in our laboratory.
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9. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 54, 7169. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
10. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 54, 7169. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
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17. For ab initio calculations on the [2,3]Wittig rearrangement, see: Wu, Y.-D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421. For relevant experimental findings, see: Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375. Tomooka, K.; Igarhashi, T.; Watanabe, M.; Nakai, T. Tetrahedron Lett. 1992, 33, 5795.
18. For ab initio calculations on the [2,3]Wittig rearrangement, see: Wu, Y.-D.; Houk, K. N.; Marshall, J. A. J. Org. Chem. 1990, 55, 1421. For relevant experimental findings, see: Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375. Tomooka, K.; Igarhashi, T.; Watanabe, M.; Nakai, T. Tetrahedron Lett. 1992, 33, 5795.
19. The program Macromodel V4.5 was employed for these calculations. Global minimum multiple conformer searching was achieved with the Monte Carlo subroutine in BATCHMIN through multiple step iterations (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 V4.5 was employed for these calculations. Global minimum multiple conformer searching was achieved with the Monte Carlo subroutine in BATCHMIN through multiple step iterations (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. Cf. Marshall, J. A.; Lebreton, J.; DeHoff, B. S.; Jenson, T. M. J. Org.Chem. 1987, 52, 3883. For a recent application, see: Hoye, T. R.; Hunpal, P. E.; Jimínez, J. I.; Mayer, M. J.; Tan, L.; Ye, Z. Tetrahedron Lett. 1994, 35, 7517.
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27. 4
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29. 3P for the isomerization of acetylenic esters and ketones to conjugated dienoates and dienones has been reported. Rychnovsky, S. D.; Kim, J. J. Org. Chem. 1994, 59, 2659. Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1992, 114, 7933.
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