Synlett 2008(6): 0837-0840  
DOI: 10.1055/s-2008-1042931
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the C14-C29 Segment of Amphidinolide U Utilizing a Tandem Dihydroxylation-SN2 Cyclization Protocol

Debendra K. Mohapatra*, Hasibur Rahaman
Organic Chemistry Division, National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25902629; e-Mail: dk.mohapatra@ncl.res.in;
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Publication History

Received 18 November 2007
Publication Date:
20 March 2008 (online)

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Abstract

The synthesis of the C14-C29 subunit of amphidinolide U is described. The key steps include the trans-2,5-disubstituted tetrahydrofurans via a highly diastereoselective and high yielding tandem dihydroxylation-SN2 cyclization, Wittig reaction, and Nozaki-Hiyama-Kishi coupling reaction.