Lipase-promoted access to phenolic herbertane-type sesquiterpenes:: (+)-1,14-herbertenediol, (-)-α-herbertenol, (-)-herbertenediol and their enantiomers

被引：11

作者：

Acherar, S

Audran, G

Fotiadu, F

Monti, H ^{[1
]}

机构：

[1] Univ Paul Cezanne, Fac Sci & Tech St Jerome, Lab Reactiv Organ Select, UMR 6180, F-13397 Marseille 20, France

[2] Univ Paul Cezanne, Fac Sci & Tech St Jerome, Lab Synth Asymmetr, UMR 6180, F-13397 Marseille 20, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 24期

关键词：

asymmetric synthesis; conformational analysis; lipases; natural products;

D O I：

10.1002/ejoc.200400395

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of (+)-1, 14-herbertenediol, and a formal enantioselective synthesis of (-)-alpha-herbertenol and (-)-herbertenediol, employing a lipase-promoted and a key stereoselective alkylation of a cyclopentane unit based methodology, are described. Molecular mechanics considerations that could account for the major role played by the substitution pattern of the benzene nucleus in the herbertane framework in comparison with those of the cuparane framework are described. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：5092 / 5099

页数：8

共 38 条

[21] 1,5-diketones from 3,4-dihydropyranones:: An application in the synthesis of (±)-α-herbertenol [J].

Harrowven, DC ;

Hannam, JC .

TETRAHEDRON, 1999, 55 (30) :9333-9340

[22] DERIVATION OF CLASS-II FORCE-FIELDS .2. DERIVATION AND CHARACTERIZATION OF A CLASS-II FORCE-FIELD, CFF93, FOR THE ALKYL FUNCTIONAL-GROUP AND ALKANE MOLECULES [J].

HWANG, MJ ;

STOCKFISCH, TP ;

HAGLER, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2515-2525

[23] Herbertane-type sesquiterpenoids from the liverwort Herbertus sakuraii [J].

Irita, H ;

Hashimoto, T ;

Fukuyama, Y ;

Asakawa, Y .

PHYTOCHEMISTRY, 2000, 55 (03) :247-253

[24] Concise asymmetric synthesis of (-)-herbertenediol [J].

Kita, Y ;

Futamura, J ;

Ohba, Y ;

Sawama, Y ;

Ganesh, JK ;

Fujioka, H .

TETRAHEDRON LETTERS, 2003, 44 (02) :411-413

[25] The rearrangement of 2,3-epoxysulfonates and its application to natural products syntheses:: Formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol [J].

Kita, Y ;

Futamura, J ;

Ohba, Y ;

Sawama, Y ;

Ganesh, JK ;

Fujioka, H .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) :5917-5924

[26] DERIVATION OF FORCE-FIELDS FOR MOLECULAR MECHANICS AND DYNAMICS FROM ABINITIO ENERGY SURFACES [J].

MAPLE, JR ;

DINUR, U ;

HAGLER, AT .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (15) :5350-5354

[27] DERIVATION OF CLASS-II FORCE-FIELDS .1. METHODOLOGY AND QUANTUM FORCE-FIELD FOR THE ALKYL FUNCTIONAL-GROUP AND ALKANE MOLECULES [J].

MAPLE, JR ;

HWANG, MJ ;

STOCKFISCH, TP ;

DINUR, U ;

WALDMAN, M ;

EWIG, CS ;

HAGLER, AT .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1994, 15 (02) :162-182

[28] 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

[29] 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

[30] Stereoselective total syntheses of (±)-1,14-herbertenediol and (±)-tochuinyl acetate and facile total syntheses of (±)-α-herbertenol, (±)-β-herbertenol and (±)-1,4-cuparenediol [J].

Paul, T ;

Pal, A ;

Gupta, PD ;

Mukherjee, D .

TETRAHEDRON LETTERS, 2003, 44 (04) :737-740

← 1 2 3 4 →