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Synthesis 2010(24): 4307-4311  
DOI: 10.1055/s-0030-1258315
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Studies on Callipeltin A: Stereoselective Synthesis of (2R,3R,4S)-3-Hydroxy-2,4,6-trimethylheptanoic Acid

Gowravaram Sabitha*, K. Yadagiri, G. Chandrashekhar, J. S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
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Publication History

Received 6 September 2010
Publication Date:
22 October 2010 (online)

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Abstract

Asymmetric synthesis of (2R,3R,4S)-3-hydroxy-2,4,6-trimethylheptanoic acid, the β-hydroxy acid unit that acylates the N-terminus of cyclic depsipeptide callipeltin A, has been devised. The approach involves the desymmetrization of a bicyclic precursor, which generates the three chiral centers.

Key words

asymmetric synthesis - callipeltin A - desymmetrization - natural products