Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 37, Pages 12228-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8043695
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Funding
- NIH [R01GM082961]
- Eli Lilly, Michigan State University
- University Distinguished Fellowship
- Dow Chemical Company Foundation
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The syntheses of haterumalides NA and NC were accomplished via the macrocyclization of a chlorovinylidene chromium carbenoid onto a pendant aldehyde to generate the C8-C9 bond with the desired stereoisomer as the major product. Utilizing the latter chemistry enables access to both C9 hydroxylated (haterumalides NC and ND) and C9 deoxygenated forms (haterumalides NA, NB, and NE; via deoxygenation of the C9-hydroxyl).
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