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Spiroketals via oxidative rearrangement of enol ethers

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

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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.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Waller, DL
Stephenson, CRJ
Wipf, Ppwipf@pitt.eduPWIPF
Date: 1 January 2007
Date Type: Publication
Journal or Publication Title: Organic and Biomolecular Chemistry
Volume: 5
Number: 1
Page Range: 58 - 60
DOI or Unique Handle: 10.1039/b612992g
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1477-0520
MeSH Headings: Alkaloids--chemical synthesis; Alkaloids--chemistry; Alkenes--chemistry; Alkenes--metabolism; Ethers, Cyclic--chemistry; Ethers, Cyclic--metabolism; Ketones--chemical synthesis; Ketones--chemistry; Molecular Structure; Oxidation-Reduction; Spiro Compounds--chemical synthesis; Spiro Compounds--chemistry; Stereoisomerism
PubMed ID: 17164906
Date Deposited: 28 Oct 2013 22:28
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/19892

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