The Novel Adamantane Isomer Tricyclo3,9>decane (2-Homotwistbrendane)

Article abstract of DOI:10.1002/hlca.19850680519

Two synthetic approaches to the novel C10H16 hydrocarbon tricyclo<4.4.0.0^3,9>decane (1; 2-homotwistbrendane), one of the 19 members of the adamantaneland, and its Lewis-acid-catalyzed rearrangement are described.One route starts from tricyclo<4.3.0.0^3,8>nonan-2-one (2; 2-twistbrendanone).The missing tenth C-atom is introduced by ring enlargement (Tiffeneau-Demjanov method).Starting from methyl 8,9,10-trinorborn-5-ene-2-endo-carboxylate (8), ring enlargement by one C-atom, regio- and stereoselective introduction of a C₁ unit to a 2-endo,6-endo-disubstituted bicyclo <3.2.1>octane, and ring closure by acyloin condensation are the key steps in the second approach.