REGIOSELECTIVITY OF 7-OXABICYCLO[2.2.1]HEPTA-2,5-DIENE-PHENOL REARRANGEMENT AS A FUNCTION OF THE ACID PROMOTER - STEREOSELECTIVE SYNTHESIS OF 1,2,3,4-TETRAHYDRO-2-HYDROXYNAPHTHALEN-2-YL METHYL KETONES

被引：15

作者：

ANTONSSON, T ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,2 RUE BARRE,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)94341-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Successive Diels-Alder additions of 1-acetylvinyl p-nitrobenzoate and didehydrobenzene to 1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1] heptane led to 5-(dimethoxymethyl)-5,12-epoxy-2-(p-nitrobenzoyloxy)-l,2,3,4-tetrahydronaphthacen-2-yl methyl ketone with high regio- and stereoselectivity. The regioselectivity of the ethereal ring opening of the 7-oxanorbornadiene moiety of the latter compound depended on the Lewis acid promotor. © 1990.

引用

页码：89 / 92

页数：4

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