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Synthesis of Monocyclic and Bicyclic Imino Sugars
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.200300079
Subject(s) - chemistry , bicyclic molecule , aldol reaction , derivative (finance) , piperidine , intramolecular force , mitsunobu reaction , ring (chemistry) , stereochemistry , alcohol , organic chemistry , catalysis , financial economics , economics
A diastereoselective aldol reaction between the chelated alanine ester enolate 5 and the protected threose derivative 6 , followed by cyclization under Mitsunobu conditions, gave the pipecolinic acid derivative 9 . This compound could easily be converted into the versatile protected derivative 11 , which could be transformed in excellent yields either into the corresponding piperidine imino sugar 14 or into the unnatural amino acid 17 . The imino alcohol 13, an intermediate in the synthesis of imino sugar 14 , was also used in a straightforward approach to indolizidinone 19 , involving an intramolecular Horner−Emmons reaction for ring‐closure. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)