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
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
收藏
页码:311 / 316
页数:6
相关论文
共 50 条
[21]   Amino acids and peptides as asymmetric organocatalysts [J].
Jarvo, ER ;
Miller, SJ .
TETRAHEDRON, 2002, 58 (13) :2481-2495
[22]   Chiral triflate technology: An efficient tool for the construction of biologically interesting natural products in optically pure forms [J].
Kotsuki, H .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (04) :334-345
[23]   A NOVEL CARBON CARBON BOND-FORMING REACTION OF TRIFLATES WITH COPPER(I)-CATALYZED GRIGNARD-REAGENTS - A NEW CONCISE AND ENANTIOSPECIFIC SYNTHESIS OF (+)-EXO-BREVICOMIN, (5R,6S)-(-)-6-ACETOXY-5-HEXADECANOLIDE, AND L-FACTOR [J].
KOTSUKI, H ;
KADOTA, I ;
OCHI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4417-4422
[24]   A general synthesis of homochiral β-hydroxy N-acetylcysteamine thioesters [J].
Le Sann, C ;
Simpson, TJ ;
Smith, DI ;
Watts, P ;
Willis, CL .
TETRAHEDRON LETTERS, 1999, 40 (21) :4093-4096
[25]   Organocatalysis: A complementary catalysis strategy advances organic synthesis [J].
List, B .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1021-1021
[26]   New mechanistic studies on the proline-catalyzed aldol reaction [J].
List, B ;
Hoang, L ;
Martin, HJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5839-5842
[27]   Proline-catalyzed asymmetric reactions [J].
List, B .
TETRAHEDRON, 2002, 58 (28) :5573-5590
[28]   Asymmetric aminocatalysis [J].
List, B .
SYNLETT, 2001, (11) :1675-1686
[29]   Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes [J].
List, B ;
Pojarliev, P ;
Castello, C .
ORGANIC LETTERS, 2001, 3 (04) :573-575
[30]   Intramolecular S-N(2) ring opening of a cyclic sulfate: Synthesis of erythro-(-)-6-acetoxy-5-hexadecanolide - A major component of mosquito oviposition attractant pheromone [J].
Lohray, BB ;
Venkateswarlu, S .
TETRAHEDRON-ASYMMETRY, 1997, 8 (04) :633-638