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Synthesis of Polyhydroxylated Aminocyclopentanes
Author(s) -
Kummeter Markus,
Kazmaier Uli
Publication year - 2003
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.200200703
Subject(s) - chemistry , enantiopure drug , dihydroxylation , ring closing metathesis , crotonaldehyde , aldol reaction , hydrolysis , organic chemistry , yield (engineering) , metathesis , stereochemistry , enantioselective synthesis , catalysis , polymer , materials science , metallurgy , polymerization
Polyhydroxylated aminocyclopentanes are an interesting class of glycosidase inhibitors. The reactions between chelated α‐allylglycine esters and crotonaldehyde gave the corresponding aldol products in good yields and selectivities. Those compounds could be converted into enantiopure polyhydroxylated aminocyclopentanes by ring‐closing metathesis, enzymatic separation and dihydroxylation. In the final deprotection step, three different protection groups were removed simultaneously in excellent yield, either by reduction or by basic hydrolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)