SYNTHESES OF 6-ACYLCOUMARINS VIA HIGHLY REGIOSELECTIVE FRIES REARRANGEMENTS - TOTAL SYNTHESES OF THE LINEAR ACYLATED COUMARINS GEIJERIN AND DEHYDROGEIJERIN

被引：11

作者：

CAIRNS, N ^{[1
]}

HARWOOD, LM ^{[1
]}

ASTLES, DP ^{[1
]}

机构：

[1] SHELL RES LTD,SITTINGBOURNE RES CTR,SITTINGBOURNE ME9 8AG,KENT,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(01)90370-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl 3-(2-acyloxy-4-methoxyphenyl)propanoates (7), prepared in high yield from 7-methoxycoumarin are key intermediates in general and efficient syntheses of 6-acylcoumarins. Under standard Fries rearrangement conditions (7) undergo highly regioselective para-migration with aluminium chloride in nitromethane. The resulting C-acylated products (8) are converted into 6-acyl-7-methoxycoumarins (4). The scope and limitations of the rearrangement and the application to the total syntheses of the natural linear acylcoumarins, geijerin (4a) and dehydrogeijerin (4b), are described.

引用

页码：7581 / 7590

页数：10

共 26 条

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