LEWIS ACID-PROMOTED DISPROPORTIONATION REACTION OF AROMATIC VINYL ETHERS AND ACETALS AND ITS APPLICATION TO THE SYNTHESIS OF PARACOTOIN

Authors
GONG YD TANAKA H IWASAWA N NARASAKA K
Citation
Yd. Gong et al., LEWIS ACID-PROMOTED DISPROPORTIONATION REACTION OF AROMATIC VINYL ETHERS AND ACETALS AND ITS APPLICATION TO THE SYNTHESIS OF PARACOTOIN, Bulletin of the Chemical Society of Japan, 71(9), 1998, pp. 2181-2185
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
71
Issue
9
Year of publication
1998
Pages
2181 - 2185
Database
ISI
SICI code
0009-2673(1998)71:9<2181:LADROA>2.0.ZU;2-#
Abstract
Aromatic vinyl ethers and acetals underwent a novel addition-fragmenta tion reaction affording olefins and esters in the presence of a Lewis acid. This reaction was applied to intramolecular cyclization reaction , giving five or six membered ring compounds in good yields. Paracotoi n, an intermediate in the biosynthesis of shikimic acid, was synthesiz ed using this cyclization reaction as the key step.