Synthesis 2014; 46(06): 817-821
DOI: 10.1055/s-0033-1338584
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Formal Synthesis of (+)-Pyrenolide D

Martin Markovič
a  Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia   Fax: +421(2)57294998   Email: [email protected]
,
Pavol Lopatka
a  Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia   Fax: +421(2)57294998   Email: [email protected]
,
Peter Koóš
b  Georganics Ltd., Koreničova 1, 811 03 Bratislava, Slovakia
,
Tibor Gracza*
a  Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia   Fax: +421(2)57294998   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 13 November 2013

Accepted after revision: 19 December 2013

Publication Date:
23 January 2014 (online)


Abstract

A concise, asymmetric formal synthesis of (+)-pyrenolide D from (E)-crotonaldehyde is described. The key steps include an enantioselective Sharpless dihydroxylation of protected hex-4-en-1-yn-3-ol and a highly diastereoselective palladium-catalysed oxycarbonylation of (2R,3S,4S)-hex-5-ene-2,3,4-triol using iron pentacarbonyl as the carbon monoxide source.

Supporting Information

 
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