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Synfacts 2020; 16(06): 0631
DOI: 10.1055/s-0040-1706999
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (±)-Periplanone B

Contributor(s):
Erick M. Carreira
,
Manuel Freis
Still WC. * Columbia University, New York, USA
(±)-Periplanone-B. Total Synthesis and Structure of the Sex Excitant Pheromone of the American Cockroach.

J. Am. Chem. Soc. 1979;
101: 2493-2495
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Publication History

Publication Date:
15 May 2020 (online)

 
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Key words

(±)-periplanone B pheromone - anionic oxy–Cope rearrangement - Rubottom oxidation - Corey–Chaykovsky reaction - Sarett oxidation

Significance

(±)-Periplanone B is a sex pheromone produced by the female American cockroach, ­Periplaneta americana, to attract male cockroaches. In 1979, Still reported the first synthesis and determined its relative configuration. His elegant synthesis relied on an anionic oxy-Cope rearrangement to form the macrocyclic ten-membered ring. After subsequent Rubottom oxidation the stage was set to introduce the epoxide groups based on the principles of macrocyclic stereocontrol.


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Comment

Divinylcyclohexenol E was obtained from enone A through a multi-step sequence. Ring expansion to cyclodecadienone F was achieved by anionic oxy-Cope rearrangement and further Rubottom oxidation. Bisepoxide J was obtained from enone G through nucleophilic epoxidation and Corey–Chaykovsky reaction. Deprotection and subsequent Sarett oxidation resulted in racemic periplanone B.


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