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: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Waller, DL | | | | Stephenson, CRJ | | | | Wipf, P | pwipf@pitt.edu | PWIPF | |
|
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-dev.library.pitt.edu/id/eprint/19892 |
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