Synthesis of C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 via "red-ox" modifications of hecogenin acetate.
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.
Lee
Seongmin
S
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Jamieson
Daniel
D
Fuchs
Philip L
PL
D002384:Catalysis; D017608:Chromium Compounds / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010619:Phenazines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*
D017608:Chromium Compounds; D010619:Phenazines; D013141:Spiro Compounds; D013256:Steroids; C454806:cephalostatin I; C505698:hecogenin acetate; C028801:chromium trioxide