SHORT, STEREOSELECTIVE SYNTHESES OF 4,5,6-TRIHYDROXYLATED NORLEUCINES - AN APPROACH TO THE SYNTHESIS OF (+)-BULGECININE

被引：20

作者：

JACKSON, RFW

RETTIE, AB

机构：

[1] Department of Chemistry, The University of Newcastle, Newcastle upon Tyne, NE1 7RU, Bedson Building

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)60500-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the L-serine derived zinc reagent 1 with D-isopropylideneglyceryl chloride gave the 4-oxo amino acid 5, which was reduced with high diastereoselectivity to give the trans-lactone 7. Analogous reaction of the D-serine derived zinc reagent gave the the 4-oxo amino acid 6, which was reduced with high diastereoselectivity to give the cis-lactone 8. Conversion of 8 to 11, the enantiomer of the Boc-protected analogue 10 of an intermediate in Fleet's synthesis of (-)-bulgecinine, was achieved in two steps.

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页码：2985 / 2986

页数：2

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