Biomimetic Transformations of Parthenolide

An investigation of BF3-mediated rearrangements of parthenolide [1] provided micheliolide [5] as a major product. Minor reaction products included 10 (14)-dehydro-5 alpha-hydroxy-trans-guaianolide [2], 9,10-dehydro-5 alpha-hydroxy-trans-guaianolide [3], the xanthanolide 2-desoxy-6-epi-parthemollin [...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1993-01, Vol.56 (1), p.90-98
Main Authors: Castañeda-Acosta, José, Fischer, Nikolaus H, Vargas, David
Format: Article
Language:English
Subjects:
Biological and medical sciences
CONTROL DE ENFERMEDADES
CONTROLE DE MALADIES
Cyclization
DISEASE CONTROL
DRUGS
EXTRACTOS VEGETALES
EXTRAIT D'ORIGINE VEGETALE
FARMACOLOGIA
General pharmacology
LACTONAS
LACTONE
LACTONES
Magnetic Resonance Spectroscopy
Medical sciences
MEDICAMENT
MEDICAMENTOS
molecular structure
PHARMACODYNAMICS
Pharmacognosy. Homeopathy. Health food
PHARMACOLOGIE
PHARMACOLOGY
Pharmacology. Drug treatments
PLANT EXTRACTS
PROPHYLAXIS
Sesquiterpenes
Sesquiterpenes, Guaiane - chemistry
SESQUITERPENOID LACTONES
SESQUITERPENOIDE
SESQUITERPENOIDS
SESQUITERPENOS
STRUCTURE
Structure-Activity Relationship
TANACETUM
TANACETUM PARTHENIUM
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Description
Summary:An investigation of BF3-mediated rearrangements of parthenolide [1] provided micheliolide [5] as a major product. Minor reaction products included 10 (14)-dehydro-5 alpha-hydroxy-trans-guaianolide [2], 9,10-dehydro-5 alpha-hydroxy-trans-guaianolide [3], the xanthanolide 2-desoxy-6-epi-parthemollin [4], 1,2-dehydro-4 alpha-hydroxyguaianolide [6], 11,13-dehydrocompressanolide [7], and bicyclo[6.2.0]dec-10(14)-en-12,6-olide [8]. Their mechanisms of formation were interpreted as rearrangements involving carbocation intermediates.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50091a013