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

Article abstract of DOI:10.1016/j.tet.2010.04.056

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.