A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation

Woo Baeg Choi, Hywyn R.O. Churchill, Joseph E. Lynch, Andrew S. Thompson, Guy R. Humphrey, R. P. Volante, Paul J. Reider, Ichiro Shinkai

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22 Scopus citations

Abstract

(3S,4S)-3[(R)-1-(t-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone 7a was prepared from (3R,4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxy)ethyl]-2-azetidinone 3 via a sequence involving coupling with 2,2,5-trimethyl-1,3-dioxan-4,6-dione 4, N-silylation, solvolysis of the methylmeldrum's acid moiety and a stereoselective acid catalyzed decarboxylation.

Original languageEnglish (US)
Pages (from-to)2275-2278
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number15
DOIs
StatePublished - Apr 11 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Choi, W. B., Churchill, H. R. O., Lynch, J. E., Thompson, A. S., Humphrey, G. R., Volante, R. P., Reider, P. J., & Shinkai, I. (1994). A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation. Tetrahedron Letters, 35(15), 2275-2278. https://doi.org/10.1016/0040-4039(94)85197-2