Total synthesis of (-)-stemospironine

被引：56

作者：

Williams, DR ^{[1
]}

Fromhold, MG ^{[1
]}

Earley, JD ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 17期

关键词：

D O I：

10.1021/ol016336a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A stereocontrolled total synthesis of the polycyclic Stemona alkaloid, (-)-stemospironine (1) has been achieved. Key transformations include the use of a Staudinger reaction leading to the aza-Wittig ring closure of the perhydroazepine system. Formation of the vicinal pyrrolidine butyrolactone is described via the stereoselective intramolecular capture of an intermediate aziridinium salt.

引用

页码：2721 / 2724

页数：4

共 44 条

[41] ASYMMETRIC TOTAL SYNTHESIS OF THE STEMONA ALKALOID (-)-STENINE [J].

WIPF, P ;

KIM, Y ;

GOLDSTEIN, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) :11106-11112

[42] STUDIES ON SOME NEW STEMONA ALKALOIDS - A DIAGNOSTICALLY USEFUL H-1-NMR LINE-BROADENING EFFECT [J].

XU, RS ;

LU, YJ ;

CHU, JH ;

IWASHITA, T ;

NAOKI, H ;

NAYA, Y ;

NAKANISHI, K .

TETRAHEDRON, 1982, 38 (17) :2667-2670

[43] STUDIES ON STEMONA ALKALOIDS .6. ALKALOIDS OF STEMONA-JAPONICA [J].

YE, Y ;

QIN, GW ;

XU, RS .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (05) :665-669

[44]

Zou C., 2000, J CHIN PHARM SCI, V9, P113

← 1 2 3 4 5 →