SYNTHESIS OF NONPEPTIDE SCAFFOLDING DOMAINS VIA A TOTALLY STEREOSELECTIVE IODOLACTONIZATION PROTOCOL

被引：17

作者：

HAUSKE, JR

JULIN, SM

机构：

[1] Central Research Division, Pfizer Inc, Groton

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)74043-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Exposure of the chiral, non-racemic, allylic ester 7 to LDA/TMSCl provides acid 8 and subsequent iodolactonization of 8 provides one lactone (9) with total stereoselectivity. X-ray analysis of the corresponding alpha-methylbenzylamides of 8 and 9 confirmed the absolute stereochemistry of the trans-anti-trans lactone (9). The synthesis is completed by treatment of 9 with the enolate of t-butyl acetate affording tetrahydrofuranyl derivative 12.

引用

页码：4909 / 4912

页数：4

共 18 条

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