LEWIS-ACID CATALYZED INTRAMOLECULAR [2-ESTER-SUBSTITUTED CONJUGATED DIENYLPHOSPHONATES AND TRIENYLPHOSPHONATES - NEW SYNTHESIS OF FUNCTIONALIZED CYCLIC TERPENOIDS(2]CYCLOADDITION OF ALPHA)

Authors
OKAUCHI T KAKIUCHI T KITAMURA N UTSUNOMIYA T ICHIKAWA J MINAMI T
Citation
T. Okauchi et al., LEWIS-ACID CATALYZED INTRAMOLECULAR [2-ESTER-SUBSTITUTED CONJUGATED DIENYLPHOSPHONATES AND TRIENYLPHOSPHONATES - NEW SYNTHESIS OF FUNCTIONALIZED CYCLIC TERPENOIDS(2]CYCLOADDITION OF ALPHA), Journal of organic chemistry, 62(24), 1997, pp. 8419-8424
Citations number
22
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
24
Year of publication
1997
Pages
8419 - 8424
Database
ISI
SICI code
0022-3263(1997)62:24<8419:LCI[CD>2.0.ZU;2-O
Abstract
alpha-Ester-substituted 1,3-dienylphosphonates 7 and 8, prepared by th e Knoevenagel condensation, underwent intramolecular [2 + 2] cycloaddi tion in the presence of Lewis acid to form bicyclo[4.2.0] (26-57% yiel d) and bicyclo[3.2.0]skeleton (14-38% yield), respectively. Similar tr eatment of homologous 1,3-dienylphosphonate 11 and 1,3,5-trienylphosph onate 12 resulted in the formation of ionone derivatives (30-94% yield ). The intramolecular cycloaddition reaction was applicable to several conjugated dienes bearing an eater group.