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

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.

SUBMITTER: Lee S

PROVIDER: S-EPMC2859694 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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

Lee Seongmin S Jamieson Daniel D Fuchs Philip L PL

Organic letters 20090101 1

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. ...[more]

PMID: 19055428

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