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. 2018 Nov 26;81(11):2364-2370.
doi: 10.1021/acs.jnatprod.8b00215. Epub 2018 Oct 30.

Total Synthesis of Violaceoid A and (-)- And (+)-Violaceoid B

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Total Synthesis of Violaceoid A and (-)- And (+)-Violaceoid B

Takatsugu Murata et al. J Nat Prod. .

Abstract

The first total synthesis of violaceoid A, a cytotoxic agent, and the asymmetric total synthesis of (-)- and (+)-violaceoid B are reported. The precursor was accessed by desymmetrization of a substituted quinol moiety, and the racemic secondary alcohol was kinetically resolved using a chiral nucleophilic catalyst. The asymmetric synthesis of (-)- and (+)-violaceoid B elucidated the absolute configuration of the naturally occurring violaceoid B. Synthetic violaceoid A inhibited the growth of human breast cancer cell lines MCF-7 and Hs 578T at concentrations of less than 100 μM, while ( S)- and ( R)-violaceoid B were inactive.

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