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Synthesis 2009(3): 474-482  
DOI: 10.1055/s-0028-1083321
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Preparation of C1-C10 and C11-O14 Fragments of Narbonolide: Exploiting the Versatility of Thiazolidinethione Chiral Auxiliary [¹]

C. Prasad Narasimhulu, Parthasarathi Das*
Discovery Research, Dr. Reddy’s Laboratories Ltd., Bollaram Road, Miyapur, Hyderabad 500 049, India
Fax: +91(40)23045438; e-Mail: parthasarathi@drreddys.com; e-Mail: parthads@yahoo.com;
Further Information

Publication History

Received 13 August 2008
Publication Date:
12 January 2009 (online)

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Abstract

An efficient stereoselective synthesis of the C1-C10 and C11-O14 fragments of narbonolide, have been accomplished by using a thiazolidinonethione as chiral auxiliary. The stereocenters at C2, C3, C4, C5, C8, and C9 in C1-C10 fragment and C12 and C13 in C11-C14 fragment were generated via asymmetric acyl-thiazolidinethione aldol reactions whereas the stereocenter at C6 was installed by means of Myers alkylation.

Key words

acyl-thiazolidinethione - aldol reaction - Crimmins protocol - Myers alkylation - Tebbe reaction

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DRL Publication No. 670.

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DRL Publication No. 670.