Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay

被引：107

作者：

Pettit, GR ^{[1
]}

Melody, N

Herald, DL

机构：

[1] Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA

[2] Arizona State Univ, Dept Chem & Biochem, Tempe, AZ 85287 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 08期

关键词：

D O I：

10.1021/jo000710n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Narciclasine (2) available in quantity from certain Amaryllidaceae species or by total synthesis was employed as a precursor for a 10-step synthetic conversion (3.6% overall yield) to natural (+)-pancratistatin (la). The key procedures involved epoxidation of natural (+)-narciclasine (2) to epoxide 6, reduction to diol 8, and formation of cyclic sulfate 12 and its ring opening with cesium benzoate followed by saponification of the benzoate to afford (+)-pancratistatin (1a).

引用

页码：2583 / 2587

页数：5

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