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Synthesis 2009(16): 2709-2714  
DOI: 10.1055/s-0029-1216903
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Studies toward a Total Synthesis of Rhizoxin D: Stereoselective Preparation of the C11-C19 Fragment [¹]

Srinivas Padakanti, Chetlur Kiran Kumar, Ettam Ashok, Parthasarathi Das*
Discovery Research, Dr. Reddy’s Laboratories Ltd., Bollaram Road, Miyapur, Hyderabad 500049, A.P., India
Fax: +91(40)23045438; e-Mail: parthasarathi@drreddys.com; e-Mail: parthads@yahoo.com;
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Publication History

Received 15 April 2009
Publication Date:
10 July 2009 (online)

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Abstract

The C11-C19 fragment of rhizoxin D was synthesized efficiently and stereoselectively. Stereoselective induction at C13 was achieved by means of the Crimmins protocol, whereas a substrate-controlled lithium aldol reaction gave the desired selectivity at the C17 position.

Key words

acyl thiazolidinone - lithium aldol reaction - Crimmins protocol - rhizoxin D

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DRL Publication No. 691.

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DRL Publication No. 691.