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The C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 has been synthesized in 11 operations from commercially available hecogenin acetate via multiple reductions and oxidations. The key transformations include (i) Cr(VI)-catalyzed E-ring opening, (ii) C17 hydroxylation, and (iii) a base-triggered cyclization cascade.

Synthesis of C14,15-Dihydro-C22,25-epi North Unit of Cephalostatin 1 via “Red-Ox” Modifications of Hecogenin Acetate