Asymmetric Formal Synthesis of (+)-Pyrenolide D

Martin Markovič; Pavol Lopatka; Peter Koóš; Tibor Gracza

doi:10.1055/s-0033-1338584

Synthesis, Table of Contents

Synthesis 2014; 46(06): 817-821
DOI: 10.1055/s-0033-1338584

paper

Asymmetric Formal Synthesis of (+)-Pyrenolide D

Authors

Martin Markovič

^aDepartment of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia Fax: +421(2)57294998 Email: tibor.gracza@stuba.sk
Pavol Lopatka

^aDepartment of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia Fax: +421(2)57294998 Email: tibor.gracza@stuba.sk
Peter Koóš

^bGeorganics Ltd., Koreničova 1, 811 03 Bratislava, Slovakia
Tibor Gracza*

^aDepartment of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia Fax: +421(2)57294998 Email: tibor.gracza@stuba.sk

Abstract

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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.

Key words

natural products - pyrenolide D - oxycarbonylation - palladium catalysis - iron pentacarbonyl

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References

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Supplementary Material

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