A synthesis of (−) supinidine and its regioisomer by intramolecular oxime olefin cycloaddition

A synthesis of (−) supinidine 1 and its regioisomer 2 from L-proline is described. The key step is a thermal intramolecular oxime-olefin cycloaddition; dimerization products resulting from intramolecular nitrone formation were also isolated. A synthesis of (−) supinidine 1 and its regioisomer 2 from...

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Bibliographic Details
Published inTetrahedron Vol. 49; no. 11; pp. 2317 - 2324
Main Authors Hassner, Alfred, Singh, Suddham, Sharma, Raman, Maurya, Rakesh
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 01.03.1993
Elsevier
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Intramolecular reaction
Alkaloid
Cycloaddition
Position isomer
Angular nitrogen heterocycle
Bicyclic compound
Proline
Aldoxime
Ethylenic compound
Enantiomer(-)
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Summary:A synthesis of (−) supinidine 1 and its regioisomer 2 from L-proline is described. The key step is a thermal intramolecular oxime-olefin cycloaddition; dimerization products resulting from intramolecular nitrone formation were also isolated. A synthesis of (−) supinidine 1 and its regioisomer 2 from L-proline is described. The key step is a thermal intramolecular oxime-olefin cycloaddition; dimerization products resulting from intramolecular nitrone formation were also isolated.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)80375-6