A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key C1-symmetric piperidine precursor. By subsequent application of RCM reactions and OsO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner.

A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines / G. Lesma, A. Colombo, N. Landoni, A. Sacchetti, A. Silvani. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:16(2007), pp. 1948-1954. [10.1016/j.tetasy.2007.07.017]

A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines

G. Lesma
Primo
;
A. Colombo
Secondo
;
N. Landoni;A. Sacchetti
Penultimo
;
A. Silvani
Ultimo
2007

Abstract

A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key C1-symmetric piperidine precursor. By subsequent application of RCM reactions and OsO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/39751
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