ALLENYL ETHERS AS PRECURSORS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND BOTRYODIPLODIN DERIVATIVES

Authors
DULCERE JP MIHOUBI MN RODRIGUEZ J
Citation
Jp. Dulcere et al., ALLENYL ETHERS AS PRECURSORS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND BOTRYODIPLODIN DERIVATIVES, Journal of organic chemistry, 58(21), 1993, pp. 5709-5716
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
21
Year of publication
1993
Pages
5709 - 5716
Database
ISI
SICI code
0022-3263(1993)58:21<5709:AEAPOA>2.0.ZU;2-N
Abstract
Beta-Bromopropargyl ethers 2a-h, 11, and 12 or allyl propargyl ethers 8d-h are easily isomerized with potassium tert-butoxide (KO-t-Bu) into the corresponding allenyl derivatives 3a-h, 13, 14, and 9d-h. These c ompounds afford alpha-methylene-gamma-butyrolactones 7a-h, 25, and 26 by application of the sequence halogenation/dehydrohalogenation/homoly tic carbocyclization. Starting from methyl vinyl ketone 1i, similar tr ansformations lead to botryodiplodin (27) or ethoxybotryodiplodin (28) .