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Synthesis 2005(16): 2777-2781  
DOI: 10.1055/s-2005-916009
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Asymmetric Synthesis of (-)-Prelactone B

Avinash A. Salaskara, Narayan V. Mayekarb, Anubha Sharmaa, Sandip K. Nayaka, Angshuman Chattopadhyayaa, Subrata Chattopadhyay*a
a Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai - 400 085, India
b Heavy Water Division, Bhabha Atomic Research Centre, Mumbai - 400 085, India
Fax: +91(22)5505151; e-Mail: schatt@apsara.barc.ernet.in;
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Publication History

Received 20 January 2005
Publication Date:
23 September 2005 (online)

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Abstract

An efficient synthesis of (-)-prelactone B has been developed using 1,2-cyclohexylidene glyceraldehyde as the chiral template. The key features of the synthesis were stereoselective crotylation of 1,2-cyclohexylidene glyceraldehyde and enantioselective reduction of a ketone, as well as operational simplicity and use of inexpensive reagents/chemicals.

Key words

chiral template - enantioselective synthesis - prelactone B