An efficient synthesis of (±)-β-herbertenol by a 1,3-cyclopentadione annelation strategy

被引：19

作者：

Chavan, SP ^{[1
]}

Kharul, RK ^{[1
]}

Kale, RR ^{[1
]}

Khobragade, DA ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 15期

关键词：

(+/-)-beta-herebertenol; Wittig reaction; reduction; annelation; xanthates;

D O I：

10.1016/S0040-4020(03)00236-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient synthesis of sesquiterpene (+/-)-beta-herebertenol is described. The formation of cyclopentadione onto the aromatic moiety is the key feature of this protocol. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2737 / 2741

页数：5

共 34 条

[1] Enantioselective synthesis of cuparane sesquiterpenes. Synthesis of (-)-cuparene and (-)-delta-cuparenol [J].

Abad, A ;

Agullo, C ;

Arno, M ;

Cunat, AC ;

Garcia, MT ;

Zaragoza, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5916-5919

[2] Enantioselective synthesis of herbertane sesquiterpenes.: Synthesis of (-)-herbertene and (-)-α-herbertenol [J].

Abad, A ;

Agulló, C ;

Cuñat, AC ;

Perni, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1741-1744

[3] CHEMOSYSTEMATICS OF BRYOPHYTES .47. TERPENOIDS AND AROMATIC-COMPOUNDS FROM SELECTED EAST MALAYSIAN LIVERWORTS [J].

ASAKAWA, Y ;

LIN, XH ;

KONDO, K ;

FUKUYAMA, Y .

PHYTOCHEMISTRY, 1991, 30 (12) :4019-4024

[4]

ASAKAWA Y, 1994, PHYTOCHEMISTRY, P1555

[5] THE INVENTION OF RADICAL REACTIONS .24. RELATIVE RATES OF ACYLATION AND RADICAL DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

DORCHAK, J ;

JASZBERENYI, JC .

TETRAHEDRON, 1992, 48 (36) :7435-7446

[6] Herbertane sesquiterpenoids from the liverworts Herbertus aduncus and H-borealis [J].

Buchanan, MS ;

Connolly, JD ;

Rycroft, DS .

PHYTOCHEMISTRY, 1996, 43 (06) :1245-1248

[7] A simple synthesis of (±)-α-cuparenone [J].

Chavan, SP ;

Patil, SS ;

Ravindranathan, T .

TETRAHEDRON, 1999, 55 (47) :13417-13422

[8] An efficient synthesis of alpha-cuparenone [J].

Chavan, SP ;

Ravindranathan, T ;

Patil, SS ;

Dhondge, VD ;

Dantale, SW .

TETRAHEDRON LETTERS, 1996, 37 (15) :2629-2630

[9] SYNTHESIS OF 7-DEOXYTAXOL AND 7,10-DIDEOXYTAXOL VIA RADICAL INTERMEDIATES [J].

CHEN, SH ;

HUANG, S ;

KANT, J ;

FAIRCHILD, C ;

WEI, JM ;

FARINA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5028-5029

[10]

CONNOLLY JD, 1991, DICT TERPENOIDS, V1, P299

← 1 2 3 4 →