Synthesis of a new ketone and alcohol with C2 symmetry; (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-onela and (S,S,S,S) tricyclo[6.3.0.03,7]undecan-2-ollb

Dissolving metal reduction of known enone S affords predominantly the racemic form of 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=91 %) was effected from ketone (+)- 13 .