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
2-oxospiro[4.5]decan-1-one
Spirolactones
Microwave irradiation
Electrocyclic reactions
Calculations
gamma-Butyrolactones
Pericyclic-reactions
Activation barriers
Reaction energetics
alpha-Methylene
Cbs-qb3 methods
Ketene acetals
Standard set
Lactones
Cyclization
γ-Butyrolactones
α-Methylene
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