6533b83afe1ef96bd12a77df

RESEARCH PRODUCT

New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4+4] cycloaddition

Bernhard WitulskiPaul A. WenderMitchell P. Croatt

subject

DieneChemistryOrganic ChemistryOxideTotal synthesisBiochemistryMedicinal chemistryCycloadditionCatalysischemistry.chemical_compoundTransition metalIntramolecular forceDrug DiscoveryOrganic chemistry

description

Studies on the viability of the type II nickel-catalyzed intramolecular [4+4] cycloaddition of bis-dienes show that it is influenced by both diene substitution and geometry. Both E- and Z-isomers of 19 and 20 react, albeit at markedly different rates, to afford cycloadducts, whereas only the Z-isomer of 9 (and not the E-isomer) reacts to give 8 and 25. Chemoselective elaboration of 8 to (±)-salsolene oxide (7) was used to confirm the cycloadduct structure while establishing a step economical route to the natural product.

yearjournalcountryeditionlanguage
2006-08-01Tetrahedron
https://doi.org/10.1016/j.tet.2006.02.085