1. Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams.
- Author
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Grainger RS, Betou M, Male L, Pitak MB, and Coles SJ
- Subjects
- Alcohols chemistry, Azabicyclo Compounds chemistry, Cyclization, Molecular Structure, Stereoisomerism, beta-Lactams chemistry, Alcohols chemical synthesis, Azabicyclo Compounds chemical synthesis, beta-Lactams chemical synthesis
- 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.
- Published
- 2012
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