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Synthesis 2011(13): 2117-2124  
DOI: 10.1055/s-0030-1260058
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Total Synthesis of (S)-Zearalenone and Zeranol

J. S. Yadav*a,b, P. Vishnu Murthya
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad - 500 607, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
b King Saud University, Riyadh 11451, Saudi Arabia
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Publication History

Received 25 March 2011
Publication Date:
26 May 2011 (online)

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Abstract

A convergent total synthesis of the naturally occurring, 14-membered macrolides (S)-zearalenone and zeranol has been achieved through application of the Diels-Alder reaction, Jacobsen kinetic resolution, Mitsunobu coupling, ring-closing metathesis, and hydrogenation as key steps.

Key words

Diels-Alder reaction - Jacobsen resolution - Mitsunobu reaction - ring-closing metathesis - macrolide

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