title: Synthesis of saframycins. X. Transformation of (-)-saframycin A to (-)-saframycin Mx type compound with the structure proposed for saframycin E.
abstract: Treatment of (-)-saframycin A (1a) with selenium oxide in acetic acid afforded (-)-saframycin G (1g), and a catalytic reduction and regioselective oxidation sequence afforded the saframycin Mx type compound (3). We applied this methodology to the transformation of (+/-)-5-hydroxysaframycin B (11) to the hydroquinone (1e). Acetylation of 1e with acetic anhydride in pyridine gave the triacetate (13), which is identical with the triacetyl derivative of natural saframycin E.
authors.affiliation: Meiji College of Pharmacy, Tokyo, Japan.
authors.forename: N
authors.initials: N
authors.lastname: Saito
authors.forename: S
authors.initials: S
authors.lastname: Harada
authors.forename: M
authors.initials: M
authors.lastname: Nishida
authors.forename: I
authors.initials: I
authors.lastname: Inouye
authors.forename: A
authors.initials: A
authors.lastname: Kubo
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D007546:Isoquinolines; C096067:saframycin E; C026925:saframycin A