Producción Científica Profesorado

Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives



Meléndez Rodríguez, Myriam

2002

M. Meléndez-Rodríguez, C. M. Cerda-García-Rojas, C. A. N. Catalán, P. Joseph-Nathan Mechanistic studies of the photochemical rearrangement of 1-oxolongipin-2-ene derivatives Tetrahedron, Volume 58, Issue 12, 18 March 2002, Pages 2331-2338. ISSNI: 0040-4020 DOI: http://dx.doi.org/10.1016/S0040-4020(02)00121-7


Abstract


Ultraviolet irradiation of (4R,5S,7S,8R,9S,10R,11R)-7,8,9-triacetyloxy-1-oxolongipin-2-ene (2) afforded the vulgarone A 7 and the pingilonene 8 derivatives as the major products, which were formed by a [1,3]-shift, together with the minor secondary photoproducts 9 and 10. The phototransformation mechanism is discussed in terms of individual ultraviolet irradiation of 7 and 8 in combination with the monitoring reaction progress of 2 by 1H NMR measurements. The stereostructures of the new carbocyclic skeleta were geometry optimized using density functional calculations.



Producto de Investigación




Artículos relacionados

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Transesterifications mediated by t-BuNH2

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Synthesis of Indolylindolines Mediated by tert-BuNH2

Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of naturalp...

Quirogane, Prenopsane, and Patzcuarane Skeletons Obtained by Photochemically Induced Molecular Rearr...

Conformationalstudies of N-carbomethoxy-2-alkoxyindolenines by dynamicNMR, crystallography, and mole...

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

First Total Synthesis of ()-Flustraminol B