SYNTHETIC STUDIES ON TAXANE CARBON FRAMEWORK - A HIGHLY EFFICIENT 8-MEMBERED RING CYCLIZATION WITH COMPLETE STEREOCONTROL

被引：24

作者：

FURUKAWA, T ^{[1
]}

MORIHIRA, K ^{[1
]}

HORIGUCHI, Y ^{[1
]}

KUWAJIMA, I ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT CHEM,TOKYO 152,JAPAN

来源：

TETRAHEDRON | 1992年 / 48卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(01)91209-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization reaction of 5-[2-(dimethoxymethyl)-6-methoxy]benzyl-2,4,4-trimethyl-3-(trimethylsilylmethyl)cyclohexenone 2 and 5-[2-(dimethoxymethyl)-6-methoxy]benzyl-2,6,6-trimethyl-3-(siloxy)-1-methylenecyclohex-2-ene 9 gave the corresponding endo tricarbocycle bearing a sp2 carbon on the bridge-head position. Phenylthio and methoxy derivatives of 9, e.g. 11 and 12, also underwent similar cyclization to afford the endo tricarbocyclic products 13 and 14 in high yields. Further, the stereochemistry of the substituents on 8-membered ring has been completely controlled in a desired manner in every case.

引用

页码：6975 / 6984

页数：10

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