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A short, stereoselective synthesis of (3R,4R)‐4‐acetoxy‐3‐[(R)‐1′(( t ‐butyldimethylsilyl)oxy) ethyl]‐2‐azetidinone, key intermediate for the preparation of carbapenem antibiotics
Author(s) -
Cozzi Franco,
Annunziata Rita,
Cinquini Mauro,
Poletti Laura,
Perboni Alcide,
Tamburini Bruno
Publication year - 1998
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.15
Subject(s) - chemistry , stereoselectivity , chirality (physics) , thienamycin , antibiotics , yield (engineering) , stereochemistry , carbapenem , combinatorial chemistry , lactam , organic chemistry , catalysis , biochemistry , materials science , metallurgy , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Abstract A short stereoselective synthesis of the acetoxy azetidinone (1), an important precursor of several biologically active β‐lactam antibiotics, has been accomplished in seven steps and 32.8% overall yield from the easily available and inexpensive (R) ethyl 3‐hydroxybutanoate. Chirality 10:91–94, 1998. © 1997 Wiley‐Liss, Inc.