The clemmensen reduction of pentacyclo [6.4.0.02,7.03,11.0 6,10]dodecane-9,12-dione

Article abstract of DOI:10.1016/S0040-4020(01)85443-0

The Clemmensen reduction of pentacyclo[6.4.0.0²,⁷.0³,¹¹.0 ⁶,¹⁰]= dodecane-9,12-dione unexpectedly led to the formation of pentacyclo[6.4.0. 0²,⁶.0⁵,⁹.0⁴, ¹²]-2-dodecanol and pentacyclo[6.4.0.0²,⁷.0³,¹¹.0 ⁶,¹⁰]dode= cane-1,8-diol as main products. Tetracyclo[6.4.0.0⁵,⁹.0⁴¹²dodecane-2,7-dione and its corresponding hemiacetal were obtained as byproduc structures of the Clemmensen products were elucidated from an extensive ¹H and ¹³C n.m.r. study.