Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 30, Pages 10286-10292Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1016975
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Funding
- NSF (CRIF) [CHE0741968]
- Teddy Traylor Fellowship, Department of Chemistry and Biochemistry, UC San Diego
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0741968] Funding Source: National Science Foundation
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The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type coupling of an oxazol-2-ylzinc reagent formed directly from the parent ethyl 2-iodooxazole-4-carboxylate by zinc insertion. Other key steps include a hetero-Diels-Alder cycloaddition to form the central embedded pyran ring, a Wittig reaction to unite Eastern and Western hemispheres, and a ring size-selective Keck macrolactonization.
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