Abstract
Hecogenin acetate 5 was converted to an intermediate suitable for construction of both “North” and “South” hexacyclic spiroketals present in cephalostatin 7. The key chemical transformations involved are: (1) the Reich iodoso syn-elimination of iodide 18; (2) Rhodium [II] catalyzed intermolecular oxygen alkylation of secondary neopentyl alcohol 21; and (3) Intramolecular Wadsworth-Emmons reaction to provide the ester precursor of aldehyde 4.
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