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Synthesis 2011(20): 3271-3276  
DOI: 10.1055/s-0030-1260214
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Expedient Stereoselective Synthesis of the Antifungal Agent (6S)-6-[(2R)-2-Hydroxy-6-phenylhexyl]-5,6-dihydro-2H-pyran-2-one

A. Venkat Narsaiah*, Ramesh S. Ghogare
Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, 500007 India
Fax: +91(40)27160387; e-Mail: vnakkirala2001@yahoo.com;
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Publication History

Received 20 June 2011
Publication Date:
08 September 2011 (online)

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Abstract

An efficient and straightforward stereoselective synthesis of (6S)-6-[(2R)-2-hydroxy-6-phenylhexyl]-5,6-dihydro-2H-pyran-2-one is described. The chiral centers were generated by Sharpless asymmetric epoxidation followed by regioselective epoxide ring opening with Red-Al to afford 1,3-diols, exclusively. All the reactions were very clean and the products were obtained in very good yields.

Keywords

Wittig reactions - epoxidations - diols - pyrans

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