Facile Synthesis of the Tricyclic Core of Sarain A. 3-Oxidopyridinium Betaine Cycloaddition Approach1

A new approach to a suitably functionalized tricyclic core of sarains has been developed by means of Katritzky's cycloaddition using 3-oxidopyridinium betaines. A key step was the regioselective differentiation of the two nearly identical hydroxy groups derived from oxidative cleavage of the do...

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Bibliographic Details
Published inOrganic letters Vol. 1; no. 12; pp. 2017 - 2019
Main Authors Sung, Moo Je, Lee, Hyoung Ik, Chong, Youhoon, Cha, Jin Kun
Format Journal Article
LanguageEnglish
Japanese
Published American Chemical Society 16.12.1999
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Summary:A new approach to a suitably functionalized tricyclic core of sarains has been developed by means of Katritzky's cycloaddition using 3-oxidopyridinium betaines. A key step was the regioselective differentiation of the two nearly identical hydroxy groups derived from oxidative cleavage of the double bond in 8 to afford 14. A stereocontrolled construction of the tricyclic core 20 of sarains containing the requisite side chain at C-3‘ was achieved by an intramolecular conjugate addition.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9911932