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| Format: | Artículo científico |
| Language: | en |
| Published: |
Sociedad Química de México
2003
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| Online Access: | https://www.redalyc.org/articulo.oa?id=47547209 |
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Table of Contents:
- Preparation of 11-Hydroxylated 11,13-Dihydrosesquiterpene Lactones Howard G. Pentes Francisco A. Macias Nikolaus H. Fischer Multidisciplinaria (Ciencias Naturales y Exactas) LDA nor enolates oxidations guaranolides Hydroxylations of the α-position of lactonic carbonylgroups of four different skeletal types (germacranolides, eudesmanolides,guaianolides, and elemanolides) of 11,13-dihydrosesquiterpenelactones were achieved by LDA-mediated generation of the correspondinglactone enolates and trapping with gaseous oxygen or with achiral oxidizing agent, (camphorylsulfonyl)oxaziridine. The oxidationswith oxygen were non-stereospecific and generated both, the 11α- and 11β-hydroxylactones in combined yields ranging from 13-47% along with norsesquiterpene ketones which are most likely formedby decomposition of the hydroperoxide anion intermediates.Hydroxylation of the germacranolide-type 11,13-dihydroparthenolidewith either (+)- or (-)-(camphorylsulfonyl)oxaziridine gave exclusivelythe 11β-hydroxylactone (66-72 %) with no detection of the norsesquiterpeneketone. 2003 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47547209 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.47