Efficient and practical synthesis of a potent anti-MRSA beta-methylcarbapenem containing a releasable side chain

Authors
Humphrey, GR Miller, RA Pye, PJ Rossen, K Reamer, RA Maliakal, A Ceglia, SS Grabowski, EJJ Volante, RP Reider, PJ
Citation
Gr. Humphrey et al., Efficient and practical synthesis of a potent anti-MRSA beta-methylcarbapenem containing a releasable side chain, J AM CHEM S, 121(49), 1999, pp. 11261-11266
Citations number
20
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
121
Issue
49
Year of publication
1999
Pages
11261 - 11266
Database
ISI
SICI code
0002-7863(199912)121:49<11261:EAPSOA>2.0.ZU;2-8
Abstract
We describe a convergent synthesis of the MRSA beta-methyl carbapenem 1, wh erein the molecule is assembled from the naphthosultam side chain 2 and the allylic carbonate of the beta-Me carbapenem piece 6. The beta-Me stereoche mistry of 6 is set up in a novel titanium enolate addition into the TBDMS a cetoxy azetidinone 5. The benzenesulfonate salt of 1 is endowed with except ional stability.