Amoenolide K and Amoenolide K 19-Acetate, Two Grindelane Peroxides from Amphiachyris amoena. Isolation, Structure Determination, and Preparation of Amoenolide K from Amoenolide A by Photochemical Oxygenation

Two new 9,13-diepoxy labdane diterpenes, amoenolide K [1] and its 19-acetate [2], were isolated from the aerial parts of the composite Amphiachyris amoena and their structures were established by spectral methods, especially high-field nmr spectroscopy. Amoenolide K [1] was prepared from amoenolide...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1995-09, Vol.58 (9), p.1407-1418
Main Authors: O'Mathúna, Dónal P, Doskotch, Raymond W
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
4-Butyrolactone - isolation & purification
CHEMICAL COMPOSITION
COMPOSICION QUIMICA
COMPOSITAE
COMPOSITION CHIMIQUE
Diterpenes - chemistry
Diterpenes - isolation & purification
DITERPENOIDE
DITERPENOIDS
DITERPENOS
ESPECTROMETRIA
Magnetic Resonance Spectroscopy
MOLECULAR CONFORMATION
Molecular Structure
Naphthols - chemistry
Naphthols - isolation & purification
Oxidation-Reduction
Peroxides - chemistry
Peroxides - isolation & purification
Photochemistry
Plants - chemistry
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
Spiro Compounds - chemistry
Spiro Compounds - isolation & purification
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Summary:Two new 9,13-diepoxy labdane diterpenes, amoenolide K [1] and its 19-acetate [2], were isolated from the aerial parts of the composite Amphiachyris amoena and their structures were established by spectral methods, especially high-field nmr spectroscopy. Amoenolide K [1] was prepared from amoenolide A [3] by singlet oxygen addition via the ene reaction. A study was made of the ene reaction products with amoenolide K triacetate [5] which showed them to arise from stereospecific oxygen addition to the 8,9-double bond, with the exception of the sterically hindered beta-side at C-9, for which no products were isolated.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50123a011