Journal
ORGANIC LETTERS
Volume 6, Issue 1, Pages 55-57Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol036092p
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- NCI NIH HHS [CA56304] Funding Source: Medline
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Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's a-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.
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