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ChemInform Abstract: Stereoselective Synthesis of Unnatural 6α-trans-2-Oxaisocephams and δ1(6)-2-Oxaisocephems.

✍ Scribed by J. I. M. HERNANDO; N. M. LASO; J. ANAYA; S. D. GERO; M. GRANDE

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereoselective Synthesis of Unnatural 6α-trans-2-Oxaisocephams and δ1(6)-2-Oxaisocephems.

-Azetidinone (III), derived from dithiyl substituted azetidinone (I), undergoes intramolecular cyclization at room temperature to give stereoselectively the title compounds (IV) and (V), which could act as precursors for compounds with possibly antibiotic activity. Attempts to perform intramolecular cyclizations between C-4 and substituents at the nitrogen of the azetidinone under ionic conditions at low temperatures (-98 to -50 • C) to give carbacephams failed. -(HERNANDO,

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