ChemInform Abstract: Synthesis and Absolute Configuration of an Optically Active Bisnoradamantane Derivative, (-)-6-Oxotricyclo[3.3.0.0^3,7]octane-2-carboxylic Acid.

ChemInform Abstract

Diels-Alder reaction of the fulvene (I) and ethyl acrylate (II) yields the bicycloheptene (IIIa). Chain elongation of (IIIa) by the usual methods gives (IIIb) in 42% overall yield from (IIIa). Using known methods, (IIIb) is converted to the acid (Va) via (IV). Optical resolution of (Va) is accomplished using (+)-1-(2-naphthyl)ethylamine (VI). The resolved acid (- )-(Va) undergoes esterification, ozonolysis and alkaline hydrolysis to yield the title compound (- )-(Vb). Wolff- Kishner reduction of (- )-(Vb) followed by esterification yields the ester ( - )-(Vc).