New route to herbertanes via a Suzuki cross-coupling reaction:: synthesis of herbertenediol

被引：18

作者：

Abad, A ^{[1
]}

Agulló, C ^{[1
]}

Cuñat, AC ^{[1
]}

Jiménez, D ^{[1
]}

Perni, RH ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 48期

关键词：

terpenes; Suzuki reactions; rearrangements; cyclopropanes;

D O I：

10.1016/S0040-4020(01)00987-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of herbertenediol, a relevant member of the herbertane-type sesquiterpene family, is described. The synthesis is based on a new general approach to this group of sesquiterpenes where the herbertane skeleton is constructed using a Suzuki cross-coupling reaction and a [2,3]-sigmatropic Still-Wittig rearrangement as key synthetic steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9727 / 9735

页数：9

共 61 条

[41] Stereospecificity of the 1,2-Wittig rearrangement: How chelation effects influence stereochemical outcome [J].

Maleczka, RE ;

Geng, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8551-8552

[42] STRUCTURE OF THE DIMETHYL SULFOXIDE OXALYL CHLORIDE REACTION-PRODUCT - OXIDATIONS OF HETEROAROMATIC AND DIVERSE ALCOHOLS TO CARBONYL-COMPOUNDS [J].

MANCUSO, AJ ;

BROWNFAIN, DS ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4148-4151

[43] STRUCTURES OF ENT-HERBERTANE SESQUITERPENOIDS DISPLAYING ANTIFUNGAL PROPERTIES FROM THE LIVERWORT HERBERTA-ADUNCA [J].

MATSUO, A ;

YUKI, S ;

NAKAYAMA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (04) :701-710

[44] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].

MIYAURA, N ;

SUZUKI, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483

[45]

NAGATA W, 1964, CHEM IND-LONDON, P1194

[46] Asymmetric [2,3]-Wittig rearrangement as a general tool for asymmetric synthesis [J].

Nakai, T ;

Tomooka, K .

PURE AND APPLIED CHEMISTRY, 1997, 69 (03) :595-600

[47]

NAKAI T, 1994, ORGANIC REACTION, V46, P106

[48]

OHE T, 1990, SYNLETT, P221

[49] Facile total synthesis of (±)-α-herbertenol, (±)-α-cuparenone and (±)-HM-1 methyl ether involving alkylation of hindered esters [J].

Pal, A ;

Gupta, PD ;

Roy, A ;

Mukherjee, D .

TETRAHEDRON LETTERS, 1999, 40 (25) :4733-4734

[50]

Rappoport Z., 1987, CHEM CYCLOPROPYL GRO, V1

← 1 2 3 4 5 6 7 →