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Published on: May 1, 2018
Synthetic study of andrastins: stereoselective construction of the BCD-ring system
Fumihiko Yoshimura1,2, Taiki Abe3, Yuichi Ishioka3
1Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan. fumi@u-shizuoka-ken.ac.jp.
Abstract:
Andrastins are meroterpenes isolated from Penicillium sp. FO-3929 that display highly potent inhibitory activities toward protein farnesyltransferase. Structurally, they possess a unique steroidal tetracyclic skeleton (the ABCD-ring) with three contiguous quaternary stereocenters on the C-ring. Herein, we describe our nitrile cyclization-based approach to the stereoselective construction of the BCD-ring system of andrastins, which contains three contiguous quaternary stereocenters on the C-ring and the correct oxidation states of the D-ring.
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