Total Synthesis of the Pseudopterane (±)-Kallolide B

Journal of Organic Chemistry

Volumn 60, Issue 4, 1995, Pages 796-797

  Marshall, James A ^a   Wallace, Eli M ^a,c   Goan, Paul S ^b,c  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b BALL STATE UNIVERSITY   (United States)

^c NIH Postdoctoral ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; KALLOLIDE B; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0028883889     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00109a007     Document Type: Article

References (27)

1. NIH Postdoctoral Fellow 1993-1995.
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4. See also: Paquette, L. A. Chemtracts-Org. Chem. 1992, 5, 141 and references cited therein.
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8. For an early example of this phenomenon, see: Still, W. C.; Mobile, D. J. Org. Chem. 1983, 48, 4785; see also ref 3b.
9. The program Macromodel V3.5 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.
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15. Swern-Wittig condensation, see: Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (2) DIBAH reduction. (3) Orthoester Claisen rearrangement. (4) DIBAH reduction. (5) Swern oxidation. See the supplementary material for details.
16. A modification of the procedure of Mukaiyama was employed: Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621.
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25. For a closely related example of such an oxidation without isomerization, see: Rayner, C. M.; Astles, P. C.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 3926.
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