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  • Title: Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams.
    Author: Grainger RS, Betou M, Male L, Pitak MB, Coles SJ.
    Journal: Org Lett; 2012 May 04; 14(9):2234-7. PubMed ID: 22512321.
    Abstract:
    The 6-azabicyclo[3.2.1]octane ring system, prevalent in a range of biologically active molecules, is prepared through a novel semipinacol rearrangement utilizing a cyclic phosphorane or sulfite intermediate. The rearrangement proceeds with exclusive N-acyl group migration of a β-lactam ring and results in carbonyl functionality at the 7- and bridging 8-position of the bicycle. Precursor ring-fused β-lactam diols are prepared through a sequence of 4-exo trig carbamoyl radical cyclization, regioselective dithiocarbamate group elimination, and dihydroxylation.
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