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Synthesis 2008(18): 2939-2942  
DOI: 10.1055/s-2008-1067218
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of (-)-6-epi-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: rajireddy@iict.res.in ;
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Publication History

Received 14 May 2008
Publication Date:
06 August 2008 (online)

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Abstract

A stereoselective total synthesis of (-)-6-epi-centro­lobine, an unnatural analogue of (-)-centrolobine, starting from readily available tri-O-acetyl-d-glucal has been described for the first time. The key steps involved in this synthetic approach are stereoselective C-glycosidation, dehydroxylation and Wittig reaction. The target molecule was achieved in nine steps with 49% overall yield.

Key words

centrolobine - tri-O-acetyl-d-glucal - C-glycosidation - dehydroxylation - Wittig reaction

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4-Benzyloxybenzyl triphenylphosphonium bromide was prepared in two steps from commercially available
p-benzyloxybenzyl alcohol using a known protocol, see ref. 4b.