ENANTIOSPECIFIC SYNTHESIS OF (-)-TABTOXININE BETA-LACTAM

被引：27

作者：

DOLLE, RE ^{[1
]}

LI, CS ^{[1
]}

NOVELLI, R ^{[1
]}

KRUSE, LI ^{[1
]}

EGGLESTON, D ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT RES LTD,DEPT MED CHEM,WELWYN GARDEN CIT AL6 9AR,HERTS,ENGLAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 01期

关键词：

D O I：

10.1021/jo00027a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent, 10-step synthesis of optically active tabtoxinine beta-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new gamma-cation amino acid synthon, (-)-4, and its use as an electrophile (3 --> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

引用

页码：128 / 132

页数：5

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