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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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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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cited_by	cdi_FETCH-LOGICAL-a288t-cc749f75b810c7c980dd7367095bb398e4ae0224d2cf05c9ffc56309201896933
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container_title	Journal of natural products (Washington, D.C.)
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creator	O'Mathúna, Dónal P Doskotch, Raymond W
description	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.
doi_str_mv	10.1021/np50123a011
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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
title	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
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