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1.
Phys Chem Chem Phys ; 16(16): 7513-20, 2014 Apr 28.
Artículo en Inglés | MEDLINE | ID: mdl-24626812

RESUMEN

The auto-oxidation of trans-1,2-disiloxybenzocyclobutene was found to be very efficient, giving endo-peroxide in quantitative yield. Each step of the mechanism of spin-forbidden addition of triplet oxygen O2((3)Σg) was studied by both EPR/spin trapping and theoretical studies.

2.
Chemistry ; 18(45): 14267-71, 2012 Nov 05.
Artículo en Inglés | MEDLINE | ID: mdl-23019072

RESUMEN

The key is symmetry! A convergent synthetic approach of the highly cytotoxic natural product (-)-callystatin A was developed assembling three fragments through Julia-Kocienski olefination and Stille cross-coupling. The new strategy relies on a pivotal local symmetry of the target molecule. In this preliminary study, particular attention was devoted to facilitate the catalytic enantiocontrol of strategic stereogenic centers present in each of the fragments (see scheme).


Asunto(s)
Ácidos Grasos Insaturados/química , Alquenos/química , Animales , Callyspongia/química , Ácidos Grasos Insaturados/síntesis química , Estereoisomerismo
3.
Org Biomol Chem ; 10(24): 4712-9, 2012 Jun 28.
Artículo en Inglés | MEDLINE | ID: mdl-22580446

RESUMEN

An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disilyloxybenzocyclobutene and the appropriate γ-alkylidenebutenolide. The feasibility and the total chemoselectivity of the [4 + 2] cycloaddition for the construction of a spirolactone moiety via an intramolecular approach (IMDA) using both partners is also described demonstrating the versatility of the γ-alkylidenebutenolide building block.


Asunto(s)
Furanos/química , Quinonas/química , Alquilación , Ciclización , Indoles/síntesis química , Estructura Molecular , Naftoquinonas/síntesis química , Espironolactona/química , Estereoisomerismo
5.
Org Biomol Chem ; 8(24): 5490-4, 2010 Dec 21.
Artículo en Inglés | MEDLINE | ID: mdl-20936215

RESUMEN

An efficient synthesis of deoxy-lambertellols was reported through a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disiloxybenzocyclobutenes and 2-methylprotoanemonine. Such transformation with δ-substituted γ-alkylidenebutenolides, to prepare new analogues of these tricyclic spirolactones, which would be very difficult to prepare by other ways, was also studied.


Asunto(s)
Furanos/química , Naftalenos/química , Quinonas/química , Compuestos de Espiro/química , Alquilación , Ciclización , Modelos Moleculares , Estructura Molecular , Factores de Tiempo
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