A highly stereoselective total synthesis of (+)-asimicin (1) is reported. The synthesis features two chelate-controlled [3 + 2] annulation reactions-one of which (e.g., 2 + 3) constitutes a key, convergent fragment assembly step-that establish all of the stereochemistry of the bis-tetrahydrofuran unit of the natural product.
Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. Publishing Authors By Initials
Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. Journal Published:
PUBLICATION TYPE: Research Support, U.S. Gov't,
Journal: Journal of the American Chemical Society
VOLUME: 127
Page Numbers: 10818-9
Journal Abbreviation: J. Am. Chem. Soc.
ISSN: 0002-7863
DAY: 10
MONTH: Aug
YEAR: 2005
Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. Information
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LANGUAGE: eng
NlmUniqueID: 7503056
Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. Keywords Mesh Terms:
KEYWORDS: Stereoisomerism
MESH TERMS: chemistry
Chemical & Substance for Abstract: Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. Information
Substance Name: bullatacin
Registry Number: 102989-24-2
Grant and Affiliation Information for Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes.
AFFILIATION: Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA.
Country: United States
AGENCY: United States NIGMS
GRANT: GM 38907
ACRONYM: GM
MEDLINETA: J Am Chem Soc
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