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(+)‐Lentiginosine, a Potent and Selective Inhibitor of Amyloglucosidase: Synthetic Efforts and Disputes on Its Absolute Configuration
Author(s) -
Cardona Francesca,
Goti Andrea,
Brandi Alberto
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600633
Subject(s) - chemistry , absolute configuration , enantioselective synthesis , stereochemistry , combinatorial chemistry , total synthesis , absolute (philosophy) , organic chemistry , catalysis , philosophy , epistemology
Abstract (+)‐Lentiginosine is a powerful and selective inhibitor of amyloglucosidases and has become a reference compound in the field among derivatives related to imino sugars. The present review focuses on the several total syntheses of this alkaloid, which rely on either a chiral pool or on enantioselective approaches that have appeared since its isolation in 1990. A summary of biological assays and molecular dynamic studies which allowed the assignment of the correct absolute configuration of natural (+)‐lentiginosine is reported.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)