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Synthesis 2010(24): 4300-4306  
DOI: 10.1055/s-0030-1258319
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© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of Rhoiptelol B

J. S. Yadav*, T. Pandurangam, V. V. Bhadra Reddy, B. V. Subba Reddy
Division of Organic Chemistry, 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 2 September 2010
Publication Date:
28 October 2010 (online)

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Abstract

A simple and efficient total synthesis of rhoiptelol B, isolated from the the leaves and fruits of Rhoiptelea chiliantha, is achieved using Sharpless asymmetric epoxidation, 1,3-anti-chiral allylation, olefin cross-metathesis, Sharpless asymmetric dihydroxylation, and ferric chloride catalyzed intramolecular SN2 cyclization as the key steps.

Key words

rhoiptelol B - Sharpless asymmetric epoxidation - allyl­ation - cross-metathesis - diarylheptanoids

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14

Compound 16 was synthesized from commercially available 4-allyl anisole in two steps (Scheme  [³] ).

Scheme 3  Reagents and conditions: (a) BBr3, CH2Cl2, -78 ˚C to r.t., 2 h, 70%; (b) TBDMSCl, imidazole, CH2Cl2, 0 ˚C to r.t., 98%.