A Facile Synthesis of Both Enantiomers of 6-Acetoxy-5-hexadecanolide, a Major Component of Mosquito Oviposition Attractant Pheromones

被引：18

作者：

Singh, Surendra ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Ctr Synth & Chem Biol, Sch Chem & Chem Biol, Dublin 4, Ireland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 12期

关键词：

Pheromones; Lactones; Natural products; Total synthesis; ASYMMETRIC ALDOL REACTIONS; CULEX-PIPENS-FATIGANS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSPECIFIC SYNTHESIS; ERYTHRO-6-ACETOXY-5-HEXADECANOLIDE; (-)-(5R; 6S)-6-ACETOXY-5-HEXADECANOLIDE; 6S)-6-ACETOXYHEXADECANOLIDE; (5R; STEREOISOMERS; CATALYST;

D O I：

10.1002/ejoc.200801134

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of (-)-(5R,6S)-erythro-6-acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone, and its enantiomer are reported. The synthesis was completed over seven steps in 28% overall yield by using Sharpless asymmetric epoxidation and ZrCl4-catalyzed cyclic acetal formation as the key steps. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1896 / 1901

页数：6

共 39 条

[1] STEREOSELECTIVE SYNTHESIS OF THE MAJOR COMPONENT OF A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE FROM A BETA-LITHIOPROPIONATE EQUIVALENT [J].

BARUA, NC ;

SCHMIDT, RR .

TETRAHEDRON, 1986, 42 (16) :4471-4474

[2] 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

[3]

BRIGGS GG, 1986, Patent No. 0194077

[4]

CHEN Z, 1994, HECHENG HUAXUE, V2, P181

[5] 5-FORMYL-DELTA-VALEROLACTONE - A USEFUL SYNTHON FOR THE CHIRAL SYNTHESIS OF THE VESPA-ORIENTALIS PHEROMONE AND THE MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE [J].

COUTROT, P ;

GRISON, C ;

BOMONT, C .

TETRAHEDRON LETTERS, 1994, 35 (45) :8381-8384

[6] Investigation of the Yamaguchi esterification mechanism. Synthesis of a Lux-S enzyme inhibitor using an improved esterification method [J].

Dhimitruka, H ;

SantaLucia, J .

ORGANIC LETTERS, 2006, 8 (01) :47-50

[7] (R)-2,3-cyclohexylideneglyceraldehyde, a novel template for stereoselective preparation of functionalized δ-lactones:: synthesis of mosquito oviposition pheromone [J].

Dhotare, B ;

Goswami, D ;

Chattopadhyay, A .

TETRAHEDRON LETTERS, 2005, 46 (37) :6219-6221

[8]

DING Y, 1992, CHINESE J CHEM, V10, P451

[9] SYNTHESIS OF THE 2 ENANTIOMERIC FORMS OF "ERYTHRO-6-ACETOXY-5-HEXADECANOLIDE, THE MAJOR COMPONENT OF A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE [J].

FUGANTI, C ;

GRASSELLI, P ;

SERVI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (22) :1285-1286

[10] SYNTHESIS OF (-)-MURICATACIN AND (-)-(5R,6S)-6-ACETOXY-5-HEXADECANOLIDE, THE MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE, FROM D-ISOASCORBIC ACID [J].

GRAVIERPELLETIER, C ;

SANIERE, M ;

CHARVET, I ;

LEMERRER, Y ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1994, 35 (01) :115-118

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