Efficient, Stereoselective Synthesis of Oxazolo[3,2-a]pyrazin-5-ones:  Novel Bicyclic Lactam Scaffolds from the Bicyclocondensation of 3-Aza-1,5-ketoacids and Amino Alcohols

The bicyclocondensation of 3-aza-1,5-ketoacids and amino alcohols furnished novel oxazolo[3,2-a]pyrazin-5-one scaffolds possessing angular, ring junction substituents in high yield with excellent levels of substrate-based diastereocontrol. Mild oxidation of serinol-derived scaffolds provided access...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2003-07, Vol.5 (15), p.2727-2730
Main Authors: Bencsik, Josef R, Kercher, Timothy, O'Sulliva, Michael, Josey, John A
Format: Article
Language:English
Subjects:
Amino Alcohols - chemistry
Aza Compounds - chemistry
Cyclization
Keto Acids - chemistry
Ketones - chemical synthesis
Lactams - chemistry
Oxazoles - chemical synthesis
Oxidation-Reduction
Propanolamines
Propylene Glycols - chemistry
Pyrazines - chemical synthesis
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The bicyclocondensation of 3-aza-1,5-ketoacids and amino alcohols furnished novel oxazolo[3,2-a]pyrazin-5-one scaffolds possessing angular, ring junction substituents in high yield with excellent levels of substrate-based diastereocontrol. Mild oxidation of serinol-derived scaffolds provided access to a new class of constrained dipeptide surrogates. Deprotection of the endocyclic amine contained within these scaffolds allows for further diversification via N-functionalization.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030065h