Journal
ORGANIC LETTERS
Volume 11, Issue 21, Pages 5086-5088Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902154p
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Funding
- University of Vermont
- Vermont Genetics Network [P20 RR16462]
- National Center for Research Resources (NCRR)
- National Institutes of Health (NIH)
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0821501] Funding Source: National Science Foundation
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An enantioselective formal total synthesis of the cytotoxic macrolide (+)-aspergillide C has been accomplished from (S)-(-)-glyceraldehyde acetonide and the Danishefsky-Kitehara diene. Strategic transformations include a hetero Diels-Alder reaction, Ferrier-type addition, and palladium-catalyzed oxidative lactonization to set key stereocenters within the dihydropyran core, followed by fragment coupling via (E)selective Julia-Kocienski olefination.
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