Intramolecular Horner-Wadsworth-Emmons reaction in base sensitive substrates: Enantiospecific synthesis of iridoid monoterpene lactones

The cyclopentapyranones (-)- 7 and (-)- 13, representing the cis -fused 9-carbon core of iridoid lactones, are synthesised from (+)-pulegone. Cyclopentapyranones (-)-1 and (-)- 2 are synthesised from R-pulegone.

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 22; pp. 3755 - 3758
Main Authors Nangia, A., Prasuna, G., Bheema Rao, P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.05.1994
Elsevier
Subjects
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Terpenoids
Iridoid
Wittig reaction
Intramolecular reaction
Ketol
Bicyclic compound
Lactone
Monoterpene
Enantiospecificity
Oxygen heterocycle
Monocyclic compound
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Summary:The cyclopentapyranones (-)- 7 and (-)- 13, representing the cis -fused 9-carbon core of iridoid lactones, are synthesised from (+)-pulegone. Cyclopentapyranones (-)-1 and (-)- 2 are synthesised from R-pulegone.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)73091-7