Synthesis from geraniol of (2E,6E,10E,14E)-16-hydroxygeranylgeraniol and some of its derivatives

被引：3
作者：
Grin'ko, M.
Kulcitki, V.
Ungur, N.
Barba, A.
Delyanu, K.
Vlad, P. F.
机构：
[1] Moldavian Acad Sci, Inst Chem, Kishinev 277028, Moldova
[2] Romanian Acad, Inst Organ Chem, Bucharest, Romania
来源：
CHEMISTRY OF NATURAL COMPOUNDS | 2007年 / 43卷 / 03期
关键词：
aliphatic diterpenoids; natural compounds; synthesis; combination reaction; alcohols;
D O I：
10.1007/s10600-007-0104-3
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Several alpha,omega-bifunctional derivatives of E,E,E-geranylgeraniol were prepared via convergent synthesis starting with geraniol (8), which was converted in three steps into the tetrahydropyranyl ether of 8-chlorogeraniol (9) and 8-hydroxygeranylphenylsulfone (10). Combination of synthons 9 and 10 with subsequent reductive removal of the phenylsulfonyl group produced the tetrahydropyranyl ether of omega-hydroxygeranylgeraniol (5), hydrolysis of which gave exclusively trans-omega-hydroxygeranylgeraniol (1). Derivatives 5-7 of geranylgeraniol were synthesized using standard methods.
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页码：277 / 281
页数：5
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