title: The revised structure, total synthesis, and absolute configuration of streptophenazine A.
abstract: A total synthesis of both diastereomers of the originally proposed structure for streptophenazine A (1) has been achieved. However, both synthetic compounds are different from the natural product. Re-examination of NMR data reported for streptophenazine A and a concise total synthesis of both diastereomers of 17 (17a and 17b) led to the structural revision of streptophenazine A to 17b. Asymmetric synthesis of (-)-streptophenazine A was also conducted, and its absolute configuration was determined to be 1'S,2'R.
authors.affiliation: Medicinal Chemistry Department, AMRI, 26 Corporate Circle, P.O. Box 15098, Albany, New York 12212-5098, USA. zhicai.yang@amriglobal.com
authors.forename: Zhicai
authors.initials: Z
authors.lastname: Yang
authors.forename: Xiaomin
authors.initials: X
authors.lastname: Jin
authors.forename: Michael
authors.initials: M
authors.lastname: Guaciaro
authors.forename: Bruce F
authors.initials: BF
authors.lastname: Molino
authors.forename: Ursula
authors.initials: U
authors.lastname: Mocek
authors.forename: Ricardo
authors.initials: R
authors.lastname: Reategui
authors.forename: Joshua
authors.initials: J
authors.lastname: Rhea
authors.forename: Tim
authors.initials: T
authors.lastname: Morley
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010619:Phenazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D010619:Phenazines; C568313:streptophenazine A