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

Christine E. Dietinger; Martin G. Banwell; Mary J. Garson; Anthony C. Willis

doi:10.1016/j.tet.2010.04.056

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

Christine E. Dietinger, Martin G. Banwell, Mary J. Garson, Anthony C. Willis

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12 Citations (Scopus)

Abstract

The octahydro-1,6-methano-IH-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 DielsAlder 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.

Original language	English
Pages (from-to)	5250-5261
Number of pages	12
Journal	Tetrahedron
Volume	66
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2010.04.056
Publication status	Published - 3 Jul 2010

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Dietinger, C. E., Banwell, M. G., Garson, M. J., & Willis, A. C. (2010). Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-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. https://doi.org/10.1016/j.tet.2010.04.056

Dietinger, Christine E. ; Banwell, Martin G. ; Garson, Mary J. et al. / Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-indene framework associated with 2-isocyanoallopupukeanane : Validation of a new synthetic strategy and the identification of enantiomeric switching regimes. In: Tetrahedron. 2010 ; Vol. 66, No. 27-28. pp. 5250-5261.

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title = "Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes",

abstract = "The octahydro-1,6-methano-IH-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 DielsAlder 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.",

keywords = "2-Isocyanoallopupukeanane, Isonitrile, Octahydro-1,6-methano- 1H-indene, Oxa-di-π-methane rearrangement, Sesquiterpenoid",

author = "Dietinger, \{Christine E.\} and Banwell, \{Martin G.\} and Garson, \{Mary J.\} and Willis, \{Anthony C.\}",

year = "2010",

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doi = "10.1016/j.tet.2010.04.056",

language = "English",

volume = "66",

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Dietinger, CE, Banwell, MG, Garson, MJ & Willis, AC 2010, 'Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes', Tetrahedron, vol. 66, no. 27-28, pp. 5250-5261. https://doi.org/10.1016/j.tet.2010.04.056

Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes. / Dietinger, Christine E.; Banwell, Martin G.; Garson, Mary J. et al.
In: Tetrahedron, Vol. 66, No. 27-28, 03.07.2010, p. 5250-5261.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-indene framework associated with 2-isocyanoallopupukeanane

T2 - Validation of a new synthetic strategy and the identification of enantiomeric switching regimes

AU - Dietinger, Christine E.

AU - Banwell, Martin G.

AU - Garson, Mary J.

AU - Willis, Anthony C.

PY - 2010/7/3

Y1 - 2010/7/3

N2 - The octahydro-1,6-methano-IH-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 DielsAlder 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.

AB - The octahydro-1,6-methano-IH-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 DielsAlder 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.

KW - 2-Isocyanoallopupukeanane

KW - Isonitrile

KW - Octahydro-1,6-methano- 1H-indene

KW - Oxa-di-π-methane rearrangement

KW - Sesquiterpenoid

UR - https://www.scopus.com/pages/publications/77954349610

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DO - 10.1016/j.tet.2010.04.056

M3 - Article

SN - 0040-4020

VL - 66

SP - 5250

EP - 5261

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -

Dietinger CE, Banwell MG, Garson MJ, Willis AC. Chemoenzymatic and enantioselective assembly of the (1α,3aβ, 6α,7aβ)- octahydro-1,6-methano-1 H-indene framework associated with 2-isocyanoallopupukeanane: Validation of a new synthetic strategy and the identification of enantiomeric switching regimes. Tetrahedron. 2010 Jul 3;66(27-28):5250-5261. doi: 10.1016/j.tet.2010.04.056

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

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