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Synthesis 2011(1): 123-126  
DOI: 10.1055/s-0030-1258341
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Tetrahydropyranyl Diarylheptanoids (-)-Centrolobine and (+)-Centrolobine

Chada Raji Reddy, Pasupulety Phani Madhavi, Srivari Chandrasekhar*
Organic Division - I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: srivaric@iict.res.in;
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Publication History

Received 30 September 2010
Publication Date:
26 November 2010 (online)

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Abstract

A versatile chiron approach to the tetrahydropyranyl diarylheptanoid natural products (-)-centrolobine and (+)-centrolobine has been described. The use of an aldol reaction followed by reductive etherification for the formation of tetrahydropyran ring is of importance.

Key words

diarylheptanoid - tetrahydropyran - centrolobine - aldol reaction - reductive etherification