Synthesis of natural oxygenated monocarbocyclic sesquiterpenoids from 6,7-epoxygeranyl acetate

被引：21

作者：

Barrero, AF ^{[1
]}

Alvarez-Manzaneda, EJ ^{[1
]}

Chahboun, R ^{[1
]}

Rivas, AR ^{[1
]}

Palomino, PL ^{[1
]}

机构：

[1] Univ Granada, Fac Ciencias, Inst Biotechnol, Dept Quim Organ, E-18071 Granada, Spain

来源：

TETRAHEDRON | 2000年 / 56卷 / 33期

关键词：

terpenes; cyclization;

D O I：

10.1016/S0040-4020(00)00560-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Natural sesquiterpenes 5-(2/,5'-epoxy-2',6',6'-trimethyl)cyclohexyl-3-methyl-1-penten-3-ol (5), cis-3-[(E)-5'-hydroxy-3'-methyl-3'-pentenyl]-2,2-dimethyl-4-methylenecyclohexanol (elegansidiol) (6), 4-(5'-acetoxy-2',6',6'-trimethyl)cyclohex-2'-enyl-3-methyl-1-penten-3-ol (7) and 5-acetoxy-3-(3-hydroxy-3-methylpent-4-enyl)2,4,4-trimethylcyclohex-2-enone (8) were prepared from 6,7-epoxygeranyl acetate (9), via (2',5'-epoxy-2',6',6'-trimethyl)cyclohexylmethyl tosylate (10), for the first time. 5 is an intermediate in the synthesis of the sesquiterpene-coumarin ether (+/-)-farnesiferol C (1). The preparation of suitable intermediates for synthesising related natural farmesiferol B (3) and D (4) is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6099 / 6113

页数：15

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