eprintid: 19892
rev_number: 16
userid: 1419
dir: disk0/00/01/98/92
datestamp: 2013-10-28 22:28:50
lastmod: 2019-02-02 15:57:01
status_changed: 2013-10-28 22:28:50
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Waller, DL
creators_name: Stephenson, CRJ
creators_name: Wipf, P
creators_email: 
creators_email: 
creators_email: pwipf@pitt.edu
creators_id: 
creators_id: 
creators_id: PWIPF
title: Spiroketals via oxidative rearrangement of enol ethers
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: A new and efficient oxidative rearrangement of alkyl enol ethers to lactone and spiroketal esters was proposed that allowed a rapid access to the common structural subunits of natural products. Additional substrates were examined including five-and six-membered diosphenol ethers and the highly functionalized hydroxy enol ether. A procedure was also developed that provided rapid access to the desired α-carbonyl functionalized cyclic ethers. Replacement of the tertiary hydroxy groups with a cyclic ether would establish an access to spiroacetals which are common features in biologically active natural products. Additional applications of this process are being explored towards biologically active molecules.
date: 2007-01-01
date_type: published
publication: Organic and Biomolecular Chemistry
volume: 5
number: 1
pagerange: 58 - 60
refereed: TRUE
issn: 1477-0520
id_number: 10.1039/b612992g
pmid: 17164906
mesh_headings: Alkaloids--chemical synthesis
mesh_headings: Alkaloids--chemistry
mesh_headings: Alkenes--chemistry
mesh_headings: Alkenes--metabolism
mesh_headings: Ethers, Cyclic--chemistry
mesh_headings: Ethers, Cyclic--metabolism
mesh_headings: Ketones--chemical synthesis
mesh_headings: Ketones--chemistry
mesh_headings: Molecular Structure
mesh_headings: Oxidation-Reduction
mesh_headings: Spiro Compounds--chemical synthesis
mesh_headings: Spiro Compounds--chemistry
mesh_headings: Stereoisomerism
chemical_names: Alkaloids
chemical_names: Alkenes
chemical_names: Ethers, Cyclic
chemical_names: Ketones
chemical_names: Spiro Compounds
chemical_names: acutumine
citation:   Waller, DL and Stephenson, CRJ and Wipf, P  (2007) Spiroketals via oxidative rearrangement of enol ethers.  Organic and Biomolecular Chemistry, 5 (1).  58 - 60.  ISSN 1477-0520     
document_url: http://d-scholarship-dev.library.pitt.edu/19892/1/licence.txt