| abstract |
A wide range of 9-methylene carbaprostacyclin analogs and homologs, and intermediates for them (~250), were prepd. from appropriate bicyclic precursors; racemic and optically active compds. were prepd. Thus, 1.1g Na- borohydride was treated with 11.6g bicyclo [3,3,0 octane-3,7-dione in 100mL ethanol and 100mL CH2CL2 to give 9.1g 7-hydroxy-bicyclo[3.3.0 octane-3-one, 0.065 mol. of which were treated with 12.8g dimethyl-tertiary-butylcyllyl chloride and 8.85g imidazole to give 2.85g 7-oxo-hydroxy-bicyclo[3.3.0 -octane-3-one-dimethyl tertiary-butylcyllyl ether and 11.8g 7-endo-hydroxy-bicyclo-[3.3.0 -octane-3-one-7-dimethyl-tertiary-butylcyllyl ether. The latter compd. in Me2CO3 was treated with Na-hydride to give I. |