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Synthesis 2010(9): 1473-1478  
DOI: 10.1055/s-0029-1218679
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation

Jhillu S. Yadav*, N. Mallikarjuna Reddy, P. Adi Narayana Reddy, Hissana Ather, Attaluri R. Prasad
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 23 November 2009
Publication Date:
19 February 2010 (online)

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Abstract

A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.

Key words

natural products - Prins cyclization - Mitsunobu reaction - macrolactonization - lactones

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8

(R)-Pent-4-en-2-ol(9) is commercially available, e.g. from Aldrich.