Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

被引：23

作者：

Beszant, S ^{[1
]}

Giannini, E ^{[1
]}

Zanoni, G ^{[1
]}

Vidari, G ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(02)00335-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1245 / 1255

页数：11

共 33 条

[1] STEREOSELECTIVE CYCLIZATION OF EPOXY ALLYLSILANES - A SYNTHESIS OF KARAHANA ETHER [J].

ARMSTRONG, RJ ;

WEILER, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (01) :214-215

[2] SYNTHESIS OF (+/-)-KARAHANA ETHER AND A (+/-)-LABDADIENOIC ACID BY THE ELECTROPHILIC CYCLIZATION OF EPOXY ALLYLSILANES [J].

ARMSTRONG, RJ ;

WEILER, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (03) :584-596

[3]

Audran G, 2001, EUR J ORG CHEM, V2001, P2293, DOI 10.1002/1099-0690(200106)2001:12<2293::AID-EJOC2293>3.0.CO

[4]

2-E

[5] NEW AND SELECTIVE REACTIONS AND REAGENTS IN CARBOHYDRATE-CHEMISTRY [J].

BARTON, DHR ;

MOTHERWELL, WB .

PURE AND APPLIED CHEMISTRY, 1981, 53 (01) :15-31

[6] ABSOLUTE-CONFIGURATION OF ENANTIOMERIC ALPHA CYCLOGERANIUM ACIDS, ALPHA CYCLOGERANIALS, ALPHA IONONES, GAMMA IONONES, ALPHA AND EPSILON CARTOTENES [J].

BUCHECKER, R ;

EGLI, R ;

REGELWIL.H ;

TSCHARNER, C ;

EUGSTER, CH ;

UHDE, G ;

OHLOFF, G .

HELVETICA CHIMICA ACTA, 1973, 56 (07) :2548-2567

[7]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1126, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1126::AID-ANIE1126>3.0.CO

[8]

2-0

[9] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].

CURRAN, DP ;

CHANG, CT .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157

[10] General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation [J].

Dahanukar, VH ;

Rychnovsky, SD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8317-8320

← 1 2 3 4 →