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Tetrahedron Letters
Volume 43, Issue 50, 9 December 2002, Pages 9019-9022
 
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doi:10.1016/S0040-4039(02)02314-6    
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Copyright © 2002 Elsevier Science Ltd All rights reserved.

Stereoselective synthesis of the fully functionalized core fragment of terpentecin

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Taotao Linga, Fatima Rivasa and Emmanuel A. TheodorakisCorresponding Author Contact Information, a, E-mail The Corresponding Author

aDepartment of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA


Received 24 September 2002; 
accepted 16 October 2002. 
Available online 9 November 2002.

Abstract

A stereoselective synthesis of the core fragment 4 of terpentecin is presented. The five contiguous asymmetric centers of 4 were prepared from enone 8 via a sequence of steps highlighted by: oxygenation of the C6 center by epoxidation of enone 18, methylenation of the C8 carbonyl group of 20 by means of the Peterson olefination, stereoselective construction of the C8 center of 21 using homogeneous catalytic hydrogenation and stereoselective oxygenation of the C7 center.

A stereoselective synthesis of the core fragment 4 of terpentecin has been accomplished starting with enone 8.

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Corresponding Author Contact InformationCorresponding author. Tel.: +1-858-822-0456; fax: +1-858-822-0386

Tetrahedron Letters
Volume 43, Issue 50, 9 December 2002, Pages 9019-9022
 
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