Investigating direct access to 2-oxospiro[4.5]decanones via 6 pi-electrocyclisation

Pouwer, Rebecca H., Schill, Heiko, Williams, Craig M. and Bernhardt, Paul V. (2007) Investigating direct access to 2-oxospiro[4.5]decanones via 6 pi-electrocyclisation. European Journal of Organic Chemistry, 2007 28: 4699-4705. doi:10.1002/ejoc.200700367

Author Pouwer, Rebecca H.
Schill, Heiko
Williams, Craig M.
Bernhardt, Paul V.
Title Investigating direct access to 2-oxospiro[4.5]decanones via 6 pi-electrocyclisation
Formatted title
Investigating direct access to 2-oxospiro[4.5]decanones via 6π-electrocyclisation
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1434-193X
Publication date 2007-10-01
Sub-type Article (original research)
DOI 10.1002/ejoc.200700367
Volume 2007
Issue 28
Start page 4699
End page 4705
Total pages 7
Place of publication Weinheim, Germany
Publisher Wiley - VCH Verlag
Language eng
Subject C1
780103 Chemical sciences
250301 Organic Chemical Synthesis
Formatted abstract
The 2-oxospiro[4.5]decan-1-one (or spiro-γ-lactone) structural motif is contained within a number of natural products, for example, the clerodane family of diterpenes. Methods to construct this structural motif are somewhat limited and usually involve multiple functional group interconversions. A novel synthetic approach to this system utilising 6π-electrocyclisation has been identified and associated density functional calculations performed. Details of the scope, limitations, and ramifications of this methodology are discussed.
Keyword Chemistry, Organic
Microwave irradiation
Electrocyclic reactions
Activation barriers
Reaction energetics
Cbs-qb3 methods
Ketene acetals
Standard set
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

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Created: Tue, 19 Feb 2008, 01:19:53 EST