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Synthesis 2010(22): 3891-3898  
DOI: 10.1055/s-0030-1258253
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convergent Synthesis of Passifloricin A via a Prins Cyclisation and Olefin Cross-Metathesis Approach

Gowravaram Sabitha*, Muddala Nagendra Prasad, Konatham Shankaraiah, Nandyala Mallikarjuna Reddy, Jhillu Singh Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
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Publication History

Received 2 August 2010
Publication Date:
17 September 2010 (online)

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Abstract

A stereoselective and convergent approach to the total synthesis of the natural product passifloricin A is illustrated using Prins cyclisation and metathesis reactions as key steps.

Key words

passifloricin A - Prins cyclisation - cross-metathesis - ring-closing metathesis - lithium aluminum hydride-lithium iodide

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3

Passifloricin A has been found to be active against some Plasmodium and Leishmania spp. (Echeverri, F. personal communication).