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.

Access to Document

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. (Principal Investigator)
Engineering & Physical Science Research Council
1/09/09 → 28/02/13
Project: Research Councils

Cite this

@article{d3d6c2fc2b9340ac960fd21cda8045c9,

title = "Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams",

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.",

author = "Grainger, {Richard S.} and Marie Betou and Louise Male and Pitak, {Mateusz B.} and Coles, {Simon J.}",

note = "MEDLINE{\textregistered} is the source for the MeSH terms of this document.",

year = "2012",

month = may,

day = "4",

doi = "10.1021/ol300605y",

language = "English",

volume = "14",

pages = "2234--2237",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams

AU - Grainger, Richard S.

AU - Betou, Marie

AU - Male, Louise

AU - Pitak, Mateusz B.

AU - Coles, Simon J.

N1 - MEDLINE® is the source for the MeSH terms of this document.

PY - 2012/5/4

Y1 - 2012/5/4

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?partnerID=yv4JPVwI&eid=2-s2.0-84860617809&md5=524e5b696f4e621247dd6ef88d756214

U2 - 10.1021/ol300605y

DO - 10.1021/ol300605y

M3 - Article

AN - SCOPUS:84860617809

SN - 1523-7060

VL - 14

SP - 2234

EP - 2237

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

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

Abstract

Bibliographical note

Access to Document

Fingerprint

Projects

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

Cite this