title: Synthesis of 23-deoxy-25-epi north unit of cephalostatin 1 via reductive and oxidative modifications of hecogenin acetate.
abstract: An efficient synthesis of the 23-deoxy-25-epi north unit of cephalostatin 1 has been achieved in 17 steps via reductive and oxidative functionalizations of hecogenin acetate with an overall yield of 3.8%. This synthesis features transetherification-mediated E-ring opening, D-ring oxidation, hemiketalization-mediated E-ring closure, and stereoselective 5/5-spiroketalization.
authors.affiliation: The Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA.
authors.forename: Rayala Naveen
authors.initials: RN
authors.lastname: Kumar
authors.affiliation: The Division of Chemical Biology and Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA. Electronic address: SeongminLee@austin.utexas.edu.
authors.forename: Seongmin
authors.initials: S
authors.lastname: Lee
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010619:Phenazines / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D010619:Phenazines; D013141:Spiro Compounds; D013256:Steroids; C454806:cephalostatin I; C505698:hecogenin acetate
keywords: Anticancer steroids; Cephalostatin; Ritterazine; Steroidal alkaloids