SYNTHETIC AND STEREOCHEMICAL STUDIES DIRECTED TOWARDS ANATOXIN-A

被引：24

作者：

HUBY, NJS ^{[1
]}

KINSMAN, RG ^{[1
]}

LATHBURY, D ^{[1
]}

VERNON, PG ^{[1
]}

GALLAGHER, T ^{[1
]}

机构：

[1] UNIV BATH, SCH CHEM, BATH BA2 7AY, AVON, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 01期

关键词：

D O I：

10.1039/p19910000145

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and stereocontrolled Ag(l)-catalysed cyclisation of a series of allenic amino esters 8a-e is described. For compounds 8a-d the cis-2,5-disubstituted pyrrolidine 9 is formed exclusively but the primary amine 8e undergoes cyclisation nonselectively to give a mixture of cis- and trans-pyrrolidines 9e and 10e. The synthetic potential of this allene-based methodology has been illustrated by the conversion of compound 8a via 9a into (+/-)-anatoxin-a 1 and the methoxy phosphine oxides 18 and 19 have been studied as ketone homologating agents within this context. The enzymatic resolution of (+/-)-8a using chymotrypsin is also described.

引用

页码：145 / 155

页数：11

共 74 条

[61] ALKYLATION AND MICHAEL ADDITIONS OF GLYCINE ETHYL-ESTER - USE IN ALPHA-AMINO-ACID SYNTHESIS AND AS ACYL CARBANION EQUIVALENT [J].