A new method for the preparation of 1,5-diynes. Synthesis of (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, the pheromone component of the cocoa pod borer moth Conopomorpha cramerella

Albán R Pereira; Jorge A Cabezas

doi:10.1021/jo048019y

A new method for the preparation of 1,5-diynes. Synthesis of (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, the pheromone component of the cocoa pod borer moth Conopomorpha cramerella

J Org Chem. 2005 Apr 1;70(7):2594-7. doi: 10.1021/jo048019y.

Authors

Albán R Pereira¹, Jorge A Cabezas

Affiliation

¹ Escuela de Química, Universidad de Costa Rica, San José, 2060, Costa Rica.

PMID: 15787548
DOI: 10.1021/jo048019y

Abstract

[reaction: see text] A new method for the synthesis of 1,5-diynes, from the reaction of 1,3-dilithiopropyne and propargyl chlorides, was developed. This new methodology was used to prepare (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, one of the pheromone components of the cocoa pod borer moth Conopomorpha cramerella, in 51% overall yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Magnetic Resonance Spectroscopy
Moths / chemistry*
Pheromones / chemical synthesis*
Pheromones / chemistry
Spectrometry, Mass, Electrospray Ionization

Substances

Pheromones