Synthesis of a New Ketone and Alcohol with C2 Symmetry; (S,S,S,S) Tricyclo3,7>undecan-2-one and (S,S,S,S) Tricyclo3,7>undecan-2-ol

Article abstract of DOI:10.1016/S0957-4166(00)86156-X

Dissolving metal reduction of known enone 5 affords predominantly the racemic form of the title ketone (3) whereas catalytic reduction gives the meso isomer 6.Neither ketone 3 nor alcohol 4 could be satisfactorily resolved.Asymmetric synthesis of (-)-3 and (+)-4 (ee=91percent) was effected from ketone (+)-13.