Lewis acid catalyzed intramolecular [2+2] cycloaddition of alpha-ester-substituted conjugated dienyl- and trienylphosphonates. New synthesis of functionalized cyclic terpenoids

被引：37

作者：

Okauchi, T ^{[1
]}

Kakiuchi, T ^{[1
]}

Kitamura, N ^{[1
]}

Utsunomiya, T ^{[1
]}

Ichikawa, J ^{[1
]}

Minami, T ^{[1
]}

机构：

[1] KYUSHU INST TECHNOL, DEPT APPL CHEM, KITAKYUSHU, FUKUOKA 804, JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 24期

关键词：

D O I：

10.1021/jo971153g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Ester-substituted 1,3-dienylphosphonates 7 and 8, prepared by the Knoevenagel condensation, underwent intramolecular [2 + 2] cycloaddition in the presence of Lewis acid to form bicyclo[4.2.0] (26-57% yield) and bicyclo[3.2.0]skeleton (14-38% yield), respectively. Similar treatment of homologous 1,3-dienylphosphonate 11 and 1,3,5-trienylphosphonate 12 resulted in the formation of ionone derivatives (30-94% yield). The intramolecular cycloaddition reaction was applicable to several conjugated dienes bearing an ester group.

引用

页码：8419 / 8424

页数：6

共 22 条

[1] FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES [J].