Synthesis of novel polycyclic, beta-lactams from D-glucose via unusual substrate-controlled radical cyclization

A highly stereoselective and substrate-controlled synthesis of polycyclic beta-lactams from D-glucose derived chiral template via intramolecular free radical cyclization is described. The cyclization is highly substrate dependant, proceeding via 6-exo and 7-endo heptynyl type radical cyclization wit...

Full description

Saved in:
Bibliographic Details
Published inSynlett no. 7; pp. 1249 - 1253
Main Authors Jayanthi, A, Puranik, VG, Deshmukh, ARAS
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.06.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tributyltin hydride
SYSTEM
azetidin-2-ones
DIASTEREOSPECIFIC SYNTHESIS
ANTIBIOTICS
radical cyclization
6-EXO-TRIG
D-MANNOSE
ANNELATION
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
polycyclic beta-lactams
STEREOCONTROLLED SYNTHESIS
PENTAACETATES
Online AccessGet more information

Cover

More Information
Summary:A highly stereoselective and substrate-controlled synthesis of polycyclic beta-lactams from D-glucose derived chiral template via intramolecular free radical cyclization is described. The cyclization is highly substrate dependant, proceeding via 6-exo and 7-endo heptynyl type radical cyclization with the radical acceptor at N-1 and the radical progenitor on a sugar moiety, anchored to the beta-lactam ring at C-4.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-822920