A stereodivergent synthesis of (+/-)-cyclophellitol and (1R,6S)-cyclophellitol from the 7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid.

被引：10

作者：

Acena, JL ^{[1
]}

deAlba, E ^{[1
]}

Arjona, O ^{[1
]}

Plumet, J ^{[1
]}

机构：

[1] UNIV COMPLUTENSE MADRID,FAC QUIM,DEPT QUIM ORGAN 1,E-28040 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 17期

关键词：

D O I：

10.1016/0040-4039(96)00464-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, stereodivergent synthesis of (+/-)-cyclophellitol 1 and its unnatural diastereoisomer (1R*,6S*)-cyclopbellitol 2 starting from the Diels-Alder adduct of furan and acrylic acid is reported. The stereochemistry of the key step (the epoxidation of alkene 3) is controlled by the nature of the hydroxyl protecting groups. (C) 1996 Elsevier Science Ltd.

引用

页码：3043 / 3044

页数：2

共 18 条

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A stereodivergent synthesis of (+/-)-cyclophellitol and (1R*,6S*)-cyclophellitol from the 7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid.

A stereodivergent synthesis of (+/-)-cyclophellitol and (1R,6S)-cyclophellitol from the 7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid.