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

被引：21

作者：

Dhotare, B ^{[1
]}

Goswami, D ^{[1
]}

Chattopadhyay, A ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 37期

关键词：

(R)-2,3-cyclohexylideneglyceraldehyde; organolithium; anti stereoselectivity; felkin-Anh model; functionalized; 6-lactones; mosquito oviposition pheromone;

D O I：

10.1016/j.tetlet.2005.07.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(R)-2,3-Cyclohexylideneglyceraldehyde 1 has been used to prepare functionalized delta-lactones. This was exemplified by a simple and efficient synthesis of the oviposition pheromone 10 of Culex pipens fatigans. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6219 / 6221

页数：3

共 42 条

[1] Unusual bioactive annonaceous acetogenins from Goniothalamus giganteus [J].

Alali, FQ ;

Rogers, L ;

Zhang, Y ;

McLaughlin, JL .

TETRAHEDRON, 1998, 54 (22) :5833-5844

[2]

Anh N.T., 1980, TOP CURR CHEM, V88, P145

[3] 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

[4] A critical outlook and comparison of enantioselective oxidation methodologies of olefins [J].

Bonini, C ;

Righi, G .

TETRAHEDRON, 2002, 58 (25) :4981-5021

[5] 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

[6] A chemoenzymatic preparation of both enantiomers of omega-hydroxymethyl-substitute lactones [J].

Buisson, D ;

Azerad, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :9-12

[7] (R)-2,3-cyclohexylideneglyceraldehyde:: A potential intermediate for convenient synthesis of 2-C-branched 2-deoxypentofuranoses [J].

Chattopadhyay, A ;

Dhotare, B ;

Hassarajani, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6874-6878

[8] (R)-2,3-O-CYCLOHEXYLIDENEGLYCERALDEHYDE, A VERSATILE INTERMEDIATE FOR ASYMMETRIC-SYNTHESIS OF CHIRAL ALCOHOL [J].

CHATTOPADHYAY, A ;

MAMDAPUR, VR .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :585-587

[9] (R)-2,3-O-cyclohexylideneglyceraldehyde, a versatile intermediate for asymmetric synthesis of homoallyl and homopropargyl alcohols in aqueous medium [J].

Chattopadhyay, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6104-6107

[10]

CHEREST M, 1968, TETRAHEDRON LETT, V9, P2205

← 1 2 3 4 5 →