Synthetic applications of the Baylis-Hillman reaction: Simple synthesis of [2E]-2-butyloct-2-enal and [2E]-2-tridecylheptadec-2-enal

被引：31

作者：

Basavaiah, D

Hyma, RS

机构：

[1] School of Chemistry, University of Hyderabad

来源：

TETRAHEDRON | 1996年 / 52卷 / 04期

关键词：

D O I：

10.1016/0040-4020(95)00955-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple synthesis of [2E]-2-butyloct-2-enal, an alarm pheromone component of the African weaver ant, Oecophylla longinoda, and [2E]-2-tridecylheptadec-2-enal, an unusual metabolite from the red alga, Laurencia species using Baylis-Hillman adducts has been described.

引用

收藏

页码：1253 / 1258

页数：6

相关论文

共 19 条

[1] SYNTHESIS OF POLYFUNCTIONAL GAMMA-LACTAMS AND PERHYDRO-1,2-PYRIDAZIN-3-ONES [J].

AMRI, H ;

ELGAIED, MM ;

BENAYED, T ;

VILLIERAS, J .

TETRAHEDRON LETTERS, 1992, 33 (48) :7345-7346

[2] VOLATILE CONSTITUENTS OF SCENT GLAND RESERVOIR OF FRUIT-SPOTTING BUG, AMBLYPELTA-NITIDA [J].

BAKER, JT ;

BLAKE, JD ;

MACLEOD, JK ;

JOHNSON, IC ;

IRONSIDE, DA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (02) :393-&

[3] A SIMPLE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXYALKANONES [J].

BASAVAIAH, D ;

GOWRISWARI, VVL .

TETRAHEDRON LETTERS, 1986, 27 (18) :2031-2032

[4] APPLICATIONS OF THE BAYLIS-HILLMAN REACTION-2 - A SIMPLE STEREOSELECTIVE SYNTHESIS OF (E)-TRISUBSTITUTED AND (Z)-TRISUBSTITUTED ALKENES [J].

BASAVAIAH, D ;

SARMA, PKS ;

BHAVANI, AKD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (09) :1091-1092

[5] APPLICATIONS OF BAYLIS-HILLMAN COUPLING PRODUCTS - A REMARKABLE REVERSAL OF STEREOCHEMISTRY FROM ESTERS TO NITRILES - A SIMPLE SYNTHESIS OF (2E)-2-METHYLALK-2-EN-1-OLS AND (2Z)-2-METHYLALK-2-ENENITRILES [J].

BASAVAIAH, D ;

SARMA, PKS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (13) :955-957

[6] THE JOHNSON-CLAISEN REARRANGEMENT OF 5-HYDROXY-2-METHYLENEALKANENITRILES - STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED TRISUBSTITUTED ALKENES [J].

BASAVAIAH, D ;

PANDIARAJU, S .

TETRAHEDRON LETTERS, 1995, 36 (05) :757-758

[7]

Baylis A. B, 1972, German Patent, Patent No. 2155113

[8] MULTICOMPONENT ALARM PHEROMONES OF WEAVER ANT [J].

BRADSHAW, JWS ;

BAKER, R ;

HOWSE, PE .

NATURE, 1975, 258 (5532) :230-231

[9] MULTICOMPONENT ALARM PHEROMONES IN THE MANDIBULAR GLANDS OF MAJOR WORKERS OF THE AFRICAN WEAVER ANT, OECOPHYLLA-LONGINODA [J].

BRADSHAW, JWS ;

BAKER, R ;

HOWSE, PE .

PHYSIOLOGICAL ENTOMOLOGY, 1979, 4 (01) :15-25

[10] GENERAL STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED ALKENES VIA STEPWISE HYDROBORATION [J].

BROWN, HC ;

BASAVAIAH, D .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5407-5409