SYNTHESIS OF A 3-KETO BICYCLIC PYRAZOLIDINONE USING A CURTIUS REARRANGEMENT

Authors
NEEL DA HOLMES RE PASCHAL JW
Citation
Da. Neel et al., SYNTHESIS OF A 3-KETO BICYCLIC PYRAZOLIDINONE USING A CURTIUS REARRANGEMENT, Tetrahedron letters, 37(28), 1996, pp. 4891-4894
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
28
Year of publication
1996
Pages
4891 - 4894
Database
ISI
SICI code
0040-4039(1996)37:28<4891:SOA3BP>2.0.ZU;2-C
Abstract
The synthesis of bicyclic pyrazolidinone 2 is described. Traditional m ethods for penem and cephem ring cyclization were found to be unsucces sful and new methodology using a Curtius rearrangement was utilized. T he 3-enamine 11 was hydrolysed to the desired beta-keto ester 2b witho ut substantial loss of the t-BOC protecting group. Copyright (C) 1996 Elsevier Science Ltd