Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones

被引：96

作者：

Manny, AJ

Kjelleberg, S

Kumar, N

deNys, R

Read, RW

Steinberg, P

机构：

[1] UNIV NEW S WALES,SCH CHEM,SYDNEY,NSW 2052,AUSTRALIA

[2] UNIV NEW S WALES,SCH MICROBIOL & IMMUNOL,SYDNEY,NSW 2052,AUSTRALIA

[3] UNIV NEW S WALES,SCH BIOL SCI,SYDNEY,NSW 2052,AUSTRALIA

来源：

TETRAHEDRON | 1997年 / 53卷 / 46期

关键词：

D O I：

10.1016/S0040-4020(97)10034-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described. (C) 1997 Elsevier Science Ltd.

引用

页码：15813 / 15826

页数：14

共 22 条

[1]

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[2] A NEW SYNTHESIS OF 3-NORMAL-BUTYL-4-BROMO-5(Z)-(BROMOMETHYLIDENE)-2-(5H)-FURANONE, A NATURALLY-OCCURRING FIMBROLIDE FROM DELISIA-FIMBRIATA (BONNEMAISONIACEAE) [J].