Facile synthesis of the tricyclic core of sarain A. 3-Oxidopyridinium betaine cycloaddition approach

[formula: see text] 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 oxidativ...

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Bibliographic Details
Published inOrganic letters Vol. 1; no. 12; pp. 2017 - 2019
Main Authors Sung, M J, Lee, H I, Chong, Y, Cha, J K
Format Journal Article
LanguageEnglish
Published United States 16.12.1999
Subjects
Animals
Betaine - chemistry
Bridged-Ring Compounds - chemical synthesis
Cyclization
Oxidation-Reduction
Porifera - chemistry
Pyridinium Compounds - chemistry
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Summary:[formula: see text] 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.
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ISSN:1523-7060
DOI:10.1021/ol9911932