Synthesis of highly functionalized tetramic acids and α-substituted pyroglutamates from L-threonine

ORGN 560

Muhammad Anwar, muhammad.anwar@chem.ox.ac.uk and Mark Moloney, mark.moloney@chem.ox.ac.uk. Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom
N-Acyl oxazolidines derived from L-threonine were subjected to diastereoselective Dieckmann cyclisation and intramolecular aldol reactions to give highly functionalised tetramic acid derivatives and α-substituted pyroglutamates respectively in good yield. The products were then deprotected under Corey's conditions to give hydroxymethyl tetramic acids and hydroxymethyl pyroglutamates in high yield. The biological activity of these compounds was evaluated against S. aureus, E. coli and B. subtilis.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006