Synthesis 2013; 45(11): 1513-1518
DOI: 10.1055/s-0033-1338432
paper
© Georg Thieme Verlag Stuttgart · New York

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

Jhillu S. Yadav*
a   Division of Organic Chemistry I, CSIR, Indian Institute of Chemical Technology, Hyderabad 500007, India   Fax: +91(40)27160512   eMail: yadavpub@iict.res.in
,
Ch. Chandravathi
b   Centre for Semiochemicals, Indian Institute of Chemical Technology, Hyderabad 500007, India
,
N. Thrimurtulu
b   Centre for Semiochemicals, Indian Institute of Chemical Technology, Hyderabad 500007, India
,
A. R. Prasad
b   Centre for Semiochemicals, Indian Institute of Chemical Technology, Hyderabad 500007, India
,
Ahmad Alkhazim Al Ghamdi
c   Engineer Abdullah Baqshan for Bee Research, King Saudi University, Saudi Arabia
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 22. Januar 2013

Accepted after revision: 28. März 2013

Publikationsdatum:
08. Mai 2013 (online)


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.