PREPARATIVE ROUTES TO SPIROACETALS DERIVED FROM CHROMAN-4-ONE (2,3-DIHYDRO-4H-1-BENZOPYRAN-4-ONE)

被引：9

作者：

CREMINS, PJ ^{[1
]}

HAYES, R ^{[1
]}

WALLACE, TW ^{[1
]}

机构：

[1] UNIV SALFORD,DEPT CHEM & APPL CHEM,SALFORD M5 4WT,LANCS,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)89903-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl 2-(4-hydroxybutyl)-4-oxo-4H-1-benzopyran-3-carboxylate 6 is transformed into the spiroacetals 13 and 14 (ratio 5: 1) via treatment with iodomediane/potassium carbonate, die process involving sequential intramolecular conjugate addition and enolate alkylation. The 2,3-epoxide 7 derived from 6 undergoes spirocyclisation to the hydroxyesters 16 and 17 upon treatment with acids. The structures of 13 and 16 were confirmed by X-ray crystallography.

引用

页码：3211 / 3220

页数：10