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

Author:
Murata, Takatsugu, Kuboki, Teppei, Ishikawa, Ryo, Saito, Takahiro, Taguchi, Shotaro, Takeuchi, Kazuma, Hatano, Emiko, Shimonaka, Motoyuki, Shiina, Isamu
Source:
Journal of natural products 2018 v.81 no.11 pp. 2364-2370
ISSN:
1520-6025
Subject:
Lewis bases, alcohols, breast neoplasms, catalysts, cytotoxicity, human cell lines, humans, moieties, neoplasm cells
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.
Agid:
6225210