Semipinacol rearrangement of Cis-fused β-lactam diols into keto-bridged bicyclic lactams
Semipinacol rearrangement of Cis-fused β-lactam diols into keto-bridged bicyclic lactams
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 beta-lactam ring and results In carbonyl functionality at the 7-and bridging 8-position of the bicycle. Precursor ring-fused beta-lactam diols are prepared through a sequence of 4-exo trig carbamoyl radical cyclization, regloselective dithiocarbamate group elimination, and dihydroxylation.
2234-2237
Grainger, Richard S.
2361f475-1635-4240-ae44-dcb1ebaaaf52
Betou, Marie
03ca73f3-c67b-442f-a54f-fcc432d97e14
Male, Louise
89b88c4f-2308-4b94-8f3a-2dc537a66533
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
18 April 2012
Grainger, Richard S.
2361f475-1635-4240-ae44-dcb1ebaaaf52
Betou, Marie
03ca73f3-c67b-442f-a54f-fcc432d97e14
Male, Louise
89b88c4f-2308-4b94-8f3a-2dc537a66533
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Grainger, Richard S., Betou, Marie, Male, Louise, Pitak, Mateusz B. and Coles, Simon J.
(2012)
Semipinacol rearrangement of Cis-fused β-lactam diols into keto-bridged bicyclic lactams.
Organic Letters, 14 (9), .
(doi:10.1021/ol300605y).
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 beta-lactam ring and results In carbonyl functionality at the 7-and bridging 8-position of the bicycle. Precursor ring-fused beta-lactam diols are prepared through a sequence of 4-exo trig carbamoyl radical cyclization, regloselective dithiocarbamate group elimination, and dihydroxylation.
This record has no associated files available for download.
More information
Published date: 18 April 2012
Identifiers
Local EPrints ID: 346007
URI: http://eprints.soton.ac.uk/id/eprint/346007
ISSN: 1523-7060
PURE UUID: bb4103a9-ce1d-44eb-ae42-e4d65f157128
Catalogue record
Date deposited: 11 Dec 2012 11:34
Last modified: 15 Mar 2024 03:01
Export record
Altmetrics
Contributors
Author:
Richard S. Grainger
Author:
Marie Betou
Author:
Louise Male
Author:
Mateusz B. Pitak
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics