SYNTHESIS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES BY REARRANGEMENTS OF CYCLOPROPYLCARBINYL SUBSTRATES

被引：14

作者：

HUDRLIK, PF ^{[1
]}

TAKACS, JM ^{[1
]}

CHOU, DTW ^{[1
]}

RUDNICK, LR ^{[1
]}

机构：

[1] RUTGERS STATE UNIV,SCH CHEM,NEW BRUNSWICK,NJ 08903

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 05期

关键词：

D O I：

10.1021/jo01319a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

α-Methylene-γ-hutvrolactones can be viewed as derivatives of homoallylic alcohols, potentially obtainable from rearrangements of cyclopropylcarbinyl derivatives. In order to test this concept, the cyclopropylcarbinyl derivatives 3a-7a were prepared. Acid-catalyzed rearrangements of 3a and 4a, solvolytic rearrangements of 5a, and AgC104-induced rearrangements of 6a and 7a gave the α-methylene-γ-butyrolactone 10 in good yields. The unsaturated substrates 3b-6b were similarly prepared and shown to rearrange to o-methylene lactone 16, showing that a suitably placed double bond can direct the regiochemistry of these rearrangements. Lactone 16 has a double bond in a position characteristic of many naturally occurring lactones. © 1979, American Chemical Society. All rights reserved.

引用

页码：786 / 793

页数：8

共 64 条

[11] TOTAL SYNTHESIS OF DL-VERNOLEPIN AND DL-VERNOMENIN [J].