Organic Letters 2009-01-01

Synthesis of C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 via "red-ox" modifications of hecogenin acetate.

Seongmin Lee, Daniel Jamieson, Philip L Fuchs

Index: Org. Lett. 11(1) , 5-8, (2009)

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Abstract

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.