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
收藏
页码：384 / 388
页数：5
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