Synthesis of (-)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol, a key precursor to inositol monophosphatase inhibitors, from (-)-quinic acid.

被引：9

作者：

Schulz, J

Gani, D

机构：

[1] UNIV ST ANDREWS,SCH CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

[2] UNIV ST ANDREWS,CTR BIOMOL SCI,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 01期

基金：

英国惠康基金; 英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(96)02229-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient route to (-)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexane-2-ol is described starting from (-)-quinic acid. The pivotal step involves a La3+-induced reversal of the diastereoselectivity for the borohydride reduction of an intermediate cyclohexan-4-one. (1R,2R,4R,6R)-6-Propyloxycyclohexan-1,2,4-triol l-phosphate, predicted to be a submicromolar inhibitor of inositol monophosphatase, was prepared from the epoxide in 20% yield and displayed the expected potency. Copyright (C) 1996 Elsevier Science Ltd

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页码：111 / 114

页数：4

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