CEPHALOSTATIN CHEMISTRY .5. CHROMIUM[II]-MEDIATED REDUCTIVE CLEAVAGE OF A TERTIARY HALIDE BEARING 3 BETA-ALKOXY GROUPS - SYNTHESIS OF THE NORTH HEXACYCLIC STEROID UNIT OF THE CEPHALOSTATIN FAMILY
Transformation of aldehyde 4 to 17nat, a hexacyclic steroid bearing the requisite functionality and spiroketal stereochemistry of the North portion of the cephalostatin family is described. The key reaction involves CrCl2 mediated reductive cleavage of a tertiary bromide which is beta to three alkoxy groups.