A short enantioselective synthesis of 3-epi-jaspine B and (+)-oxybiotin via an intramolecular tandem desilylation oxa-Michael addition strategy

A new synthesis of cytotoxic anhydrophytosphingosine 3- epi -jaspine B (34.7% overall yield; 97% ee) and (+)-oxybiotin (21.2% overall yield; 97% ee), bioactive oxygen analogue of biotin, is described starting from commercially available cis -2-butene-1,4-diol. The key reactions employed in the synth...

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Bibliographic Details
Published inRSC advances Vol. 4; no. 91; pp. 49770 - 49774
Main Authors Shelke, Anil M., Rawat, Varun, Sudalai, Arumugam, Suryavanshi, Gurunath
Format Journal Article
LanguageEnglish
Published 2014
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Summary:A new synthesis of cytotoxic anhydrophytosphingosine 3- epi -jaspine B (34.7% overall yield; 97% ee) and (+)-oxybiotin (21.2% overall yield; 97% ee), bioactive oxygen analogue of biotin, is described starting from commercially available cis -2-butene-1,4-diol. The key reactions employed in the synthesis include Sharpless asymmetric epoxidation and a novel tandem desilylation oxa-Michael addition reaction strategy to construct a tetrahydrofuran core (dr >99%).
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA08698H