Chemoenzymatic and enantioselective assembly of the (1 alpha,3a beta,6 alpha,7a beta)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switch

Dietinger, Christine E., Banwell, Martin G., Garson, Mary J. and Willis, Anthony C. (2010) Chemoenzymatic and enantioselective assembly of the (1 alpha,3a beta,6 alpha,7a beta)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes. Tetrahedron, 66 27-28: 5250-5261. doi:10.1016/j.tet.2010.04.056


Author Dietinger, Christine E.
Banwell, Martin G.
Garson, Mary J.
Willis, Anthony C.
Title Chemoenzymatic and enantioselective assembly of the (1 alpha,3a beta,6 alpha,7a beta)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes
Formatted title
Chemoenzymatic and enantioselective assembly of the (1α,3aß,6α,7aß) -octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2010-07-03
Sub-type Article (original research)
DOI 10.1016/j.tet.2010.04.056
Volume 66
Issue 27-28
Start page 5250
End page 5261
Total pages 12
Place of publication Oxford, U.K.
Publisher Pergamon
Collection year 2011
Language eng
Formatted abstract
The octahydro-1,6-methano-1H-indene framework associated with the marine sesquiterpenoid 2-iso-cyanoallopupukeanane (1) has been prepared in enantiomerically pure form from the cis-1,2-dihy-drocatechol 8 using Dielse-Alder cycloaddition, oxa-di-π-methane rearrangement and intramolecular enolate alkylation steps as the key bond-forming events. Three distinct strategies for employing such sequences in the selective synthesis of either enantiomeric form of the target framework have been identified.
© 2010 Elsevier Ltd. All rights reserved.
Keyword 2-Isocyanoallopupukeanane
Isonitrile
Octahydro-1,6-methano-1H-indene
Oxa-di-pi-methane rearrangement
Sesquiterpenoid
Alpha-heterosubstituted ketones
Bioactive marine metabolites
Taxane diterpene synthesis
Lithium amide bases
Asymmetric-synthesis
Natural-products
Axinyssa N.sp
Biosynthesis
Sesquiterpene
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Sun, 11 Jul 2010, 00:00:50 EST