Synthesis, characterization and antiproliferative activity of β-aryl-ω-iodo-γ-lactones
A convenient pathway for the synthesis of new of β-aryl-ω-iodo- γ-lactones is described. The synthetic route led to both cis and trans isomers which were separated by column chromatography or crystallization. The structures of synthesized compounds were confirmed by spectroscopic methods: IR, NMR and HR-MS. For lactones with naphthyl ring (6e and 7e) the crystal structures were also obtained. The lactones were screened for biological evaluation against cancer line HL-60 (human promyelocytic leukemia). The tests showed that the presence of substituent at the benzene ring does not significantly affect the antiproliferative activity of the compound.
Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide
The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.
An unusual β-vinyl effect leading to high efficiency and enantioselectivity of the amidase, nitrile biotransformations for the preparation of enantiopure 3-arylpent-4-enoic acids and amides and their applications in synthesis
(Chemical Equation Presented) Biotransformations of 3-arylpent-4- enenitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst were studied, and an unusual β-vinyl effect of the substrate on
Regio- and enantio-selective allylic alkylation catalysed by a chiral monophosphine-palladium complex
Allylic alkylation of racemic 1-arylprop-2-enyl acetates [ArCH(OAc)CH=CH2] with the sodium enolate of dimethyl methylmalonate in the presence of a palladium catalyst coordinated with (R)-2-diphenylphosphino-2′-methoxy-1,1′-binaphthyl [(R)-MeO-MOP] proceeds with high branch selectivity (90%) to give chiral products [ArC*H-(Nu)CH=CH2] of up to 87% ee.
Hayashi, Tamio,Kawatsura, Motoi,Uozumi, Yasuhiro
p. 561 - 562
(2007/10/03)
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