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Synthesis 2009(19): 3301-3304  
DOI: 10.1055/s-0029-1216936
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise and Efficient Synthesis of (5R,7S)-Kurzilactone and Its (5S,7R)-Enantiomer by the Mukaiyama Aldol Reaction

Gowravaram Sabitha*, Peddabuddi Gopal, C. Nagendra Reddy, Jhillu S. Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com ;
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Publication History

Received 8 May 2009
Publication Date:
14 August 2009 (online)

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Abstract

Natural kurzilactone (5R,7S) and its (5S,7R)-enantiomer were synthesized by a convergent approach using a diastereoselective Mukaiyama aldol reaction to construct the anti diol unit. Finally, a ring-closing metathesis reaction led to the target molecule.

Key words

kurzilactone - Mukaiyama reaction - aldol reaction - ring closure - metathesis

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