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Synthesis of Isosteric Analogues of Acylglycosylglycerols Active as Chemoprevention Agents
Author(s) -
Compostella Federica,
Colombo Diego,
Ferraboschi Patrizia,
Scala Antonio,
Toma Lucio,
Ronchetti Fiamma
Publication year - 2002
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 - 10.1002/1099-0690(200204)2002:8<1429::aid-ejoc1429>3.0.co;2-2
Subject(s) - chemistry , synthon , stereochemistry , regioselectivity , ketone , moiety , ether , anomer , combinatorial chemistry , organic chemistry , catalysis
Monoacylated glycosylglycerols are known anti‐tumor promoters: in order to study the role of the ester function in the modulation of their activity, we synthesized several analogues in which the acyloxy moiety was substituted with isosteric chains linked to the glycosylglycerol skeleton through an ether or a ketone functionality or simply by a C−C bond. Depending on the position of the chain, the key steps in the synthesis were either the coupling of suitable chiral synthons with the sugar, with complete stereocontrol over the anomeric configuration, or regioselective elaboration at position 6 of the sugar. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)