Synthesis of (-)-(5R,6S)-6-acetoxyhexadecanolide based on L-proline-catalyzed asymmetric aldol reactions

被引：42

作者：

Ikishima, H ^{[1
]}

Sekiguchi, Y ^{[1
]}

Ichikawa, Y ^{[1
]}

Kotsuki, H ^{[1
]}

机构：

[1] Kochi Univ, Fac Sci, Lab Nat Prod Synth, Kochi 7808520, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

关键词：

proline; aldol; aldehydes; oviposition attractant pheromone;

D O I：

10.1016/j.tet.2005.08.111

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method for proline-catalyzed asymmetric aldol reactions using synthons of straight-chain aliphatic aldehydes, and aldehydes bearing a 1,3-dithiane moiety at the beta-position, has been developed. This method was successfully applied to the synthesis of (5R,6S)-6-acetoxyhexadecanolide, an oviposition attractant pheromone of the female Culex mosquito. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：311 / 316

页数：6

共 50 条

[1] Isolation of West Nile virus from mosquitoes, crows, and a Cooper's hawk in Connecticut [J].

Anderson, JF ;

Andreadis, TG ;

Vossbrinck, CR ;

Tirrell, S ;

Wakem, EM ;

French, RA ;

Garmendia, AE ;

Van Kruiningen, HJ .

SCIENCE, 1999, 286 (5448) :2331-2333

[2] Density functional theory study of the mechanism of the proline-catalyzed intermolecular aldol reaction [J].

Arnó, M ;

Domingo, LR .

THEORETICAL CHEMISTRY ACCOUNTS, 2002, 108 (04) :232-239

[3] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[4] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[5]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[6] ENANTIO AND STEREOSELECTIVE SYNTHESIS OF (5R,6S)-6-ACETOXYHEXADECANOLIDE, A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE [J].

BONINI, C ;

CHECCONI, M ;

RIGHI, G ;

ROSSI, L .

TETRAHEDRON, 1995, 51 (14) :4111-4116

[7] Asymmetric aldol reactions in poly(ethylene glycol) catalyzed by L-proline [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Reddy, NR ;

Sultana, SS .

TETRAHEDRON LETTERS, 2004, 45 (23) :4581-4582

[8] Computational evidence for the enamine mechanism of intramolecular Aldol reactions catalyzed by proline [J].

Clemente, FR ;

Houk, KN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5766-5768

[9] Direct organocatalytic aldol reactions in buffered aqueous media [J].

Córdova, A ;

Notz, W ;

Barbas, CF .

CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025

[10]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

← 1 2 3 4 5 →