Synthetic study of andrastins: stereoselective construction of the BCD-ring system

被引：1

作者：

Yoshimura, Fumihiko ^{[1
,2
]}

Abe, Taiki ^{[3
]}

Ishioka, Yuichi ^{[3
]}

Tanino, Keiji ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

[2] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka 4228526, Japan

[3] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0600810, Japan

来源：

JOURNAL OF ANTIBIOTICS | 2019年 / 72卷 / 06期

基金：

日本学术振兴会;

关键词：

PROTEIN FARNESYLTRANSFERASE INHIBITORS; PENICILLIUM SP FO-3929; DIELS-ALDER;

D O I：

10.1038/s41429-018-0136-x

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

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.

引用

页码：384 / 388

页数：5

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