In this review we describe the asymmetrization of readily available C-S-symmetric compounds by enzyme-catalyzed reactions to provide chiral building blocks for the effective enantioselective synthesis of certain indole and quinolizidine alkaloids. By the asymmetrization of 1,2-disubstituted cycle cyclohex-4-enes a series of class I alkaloids, such as (-)-antirhine, (-)-akagerine, and (+)-meroquinene, have been synthesized from the relevant chiral precursors. By employing the same chemo-enzymatic approach, asymmetrization of C-S-symmetric 3,5-disubstituted piperidines provides access to 15,20-dihydrocleavamine and its analogues, as well as to (+)-tacamonine. The synthetic design and details of the various syntheses are presented. In addition, the scope and prospects of the symmetrization-asymmetrization strategy are discussed with special reference to the quinolizidine alkaloids.
A chemo-enzymatic approach to some indole and quinolizidine alkaloids from C-s-symmetric precursors / B. Danieli, G. Lesma, D. Passarella, A. Silvani. - In: CURRENT ORGANIC CHEMISTRY. - ISSN 1385-2728. - 4:2(2000), pp. 231-261.
|Titolo:||A chemo-enzymatic approach to some indole and quinolizidine alkaloids from C-s-symmetric precursors|
DANIELI, BRUNO (Primo)
LESMA, GIORDANO (Secondo)
PASSARELLA, DANIELE (Penultimo)
SILVANI, ALESSANDRA (Ultimo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2000|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.2174/1385272003376328|
|Appare nelle tipologie:||01 - Articolo su periodico|