Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams

Richard S. Grainger; Marie Betou; Louise Male; Mateusz B. Pitak; Simon J. Coles

doi:10.1021/ol300605y

Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams

Richard S. Grainger, Marie Betou, Louise Male, Mateusz B. Pitak, Simon J. Coles

Chemistry

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2234-2237
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	9
Early online date	18 Apr 2012
DOIs	https://doi.org/10.1021/ol300605y
Publication status	Published - 4 May 2012

Bibliographical note

MEDLINE® is the source for the MeSH terms of this document.

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10.1021/ol300605yLicence: None: All rights reserved

Rearrangement of cis-fused beta-lactams into the 6-azabicyclo(3.2.1) octane ring system
Grainger, R.
Engineering & Physical Science Research Council
1/09/09 → 28/02/13
Project: Research Councils

Cite this

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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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AU - Pitak, Mateusz B.

AU - Coles, Simon J.

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AB - 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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Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams

Abstract

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Rearrangement of cis-fused beta-lactams into the 6-azabicyclo(3.2.1) octane ring system

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