A Practical Total Synthesis of Both E- and Z-Isomers of Optically Pure 
(S)-14-Methylhexadec-8-enal (Trogodermal)

Jhillu S. Yadav; Ch. Chandravathi; N. Thrimurtulu; A. R. Prasad; Ahmad Alkhazim Al Ghamdi

doi:10.1055/s-0033-1338432

Synthesis, Table of Contents

Synthesis 2013; 45(11): 1513-1518
DOI: 10.1055/s-0033-1338432

paper

A Practical Total Synthesis of Both E- and Z-Isomers of Optically Pure (S)-14-Methylhexadec-8-enal (Trogodermal)

Jhillu S. Yadav*

^aDivision of Organic Chemistry I, CSIR, Indian Institute of Chemical Technology, Hyderabad 500007, India Fax: +91(40)27160512 Email: yadavpub@iict.res.in

,

Ch. Chandravathi

^bCentre for Semiochemicals, Indian Institute of Chemical Technology, Hyderabad 500007, India

,

N. Thrimurtulu

^bCentre for Semiochemicals, Indian Institute of Chemical Technology, Hyderabad 500007, India

,

A. R. Prasad

^bCentre for Semiochemicals, Indian Institute of Chemical Technology, Hyderabad 500007, India

,

Ahmad Alkhazim Al Ghamdi

^cEngineer Abdullah Baqshan for Bee Research, King Saudi University, Saudi Arabia

› Author Affiliations

Abstract

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Abstract

The total synthesis of both E- and Z-isomers of optically pure (S)-14-methylhexadec-8-enal (trogodermal) is described. Key steps involved Corey–Fuchs reaction, zipper isomerization, and different hydrogenation conditions for cis- and trans-isomers.

Key words

sex pheromone - trogodermal - (R)-citronellol - Corey–Fuchs reaction - zipper isomerization

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References

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