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Synthesis 2010(21): 3657-3662  
DOI: 10.1055/s-0030-1258244
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of (3R,5R)-5-Hydroxy-de-O-methyllasiodiplodin via the Prins Cyclization

Jhillu S. Yadav*, N. Thrimurtulu, Md. Ataur Rahman, J. Satyanarayana Reddy, A. R. Prasad, B. V. Subba Reddy
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 5 July 2010
Publication Date:
07 September 2010 (online)

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Abstract

A practical stereoselective total synthesis of (3R,5R)-5-hydroxy-de-O-methyllasiodiplodin has been accomplished via Prins cyclization. It exhibits potato microtuber inducing activity. The synthetic sequence involves Prins cyclization, reductive opening of the pyran ring, esterification, and ring-closing metathesis (RCM) as the key steps.

Key words

Prins cyclization - ring-closing metathesis - esterification - reductive ring opening - lactone