Synthesis of natural oxygenated monocarbocyclic sesquiterpenoids from 6,7-epoxygeranyl acetate
Synthesis of natural oxygenated monocarbocyclic sesquiterpenoids from 6,7-epoxygeranyl acetate
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DOI：
10.1016/s0040-4020(00)00560-3
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发表时间：
2000-08-11
期刊：
影响因子：
2.1
通讯作者：
Palomino, PL
中科院分区：
文献类型：
--
作者：
Barrero, AF;Alvarez-Manzaneda, EJ;Palomino, PL
天然倍半萜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’-乙酰氧基-2‘，6’，6‘-trimethyl)cyclohex-2’-enyl-3-methyl-1-penten-3-ol(7)和5-acetoxy-3-(3-hydroxy-3-methylpent-4-enyl)2，4，4-trimethylcyclohex-2-enone(8)是由6，7-环氧基香叶乙酸酯(9)通过(2‘，5’-epoxy-2‘，6’，6‘-trimethyl)cyclohexylmethyl对甲苯磺酸盐(10)首次合成的。5是倍半萜-香豆素醚(+/-)-法尼西尔醇C(1)合成的中间体。还报道了合成相关的天然法马西酚B(3)和D(4)的合适中间体的制备。(C)2000爱思唯尔科学有限公司。保留所有权利。
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.