title: A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone.
abstract: A novel and efficient method of stereoselectively introducing α-nitromethyl group to C-7 position of 11α-hydroxyl canrenone 4 was described. In addition, this method was successfully applied in a total synthesis of Eplerenone 8. The route was characteristic of simple operation, moderate reaction conditions with 5 steps and 55% total yield, at the same time, without any expensive or toxic reagent in use.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Science, 555 Zu Cong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China.
authors.forename: Bin
authors.initials: B
authors.lastname: Zhang
authors.forename: Hongli
authors.initials: H
authors.lastname: Chen
authors.forename: Huanyu
authors.initials: H
authors.lastname: Tang
authors.forename: Huijin
authors.initials: H
authors.lastname: Feng
authors.forename: Yuanchao
authors.initials: Y
authors.lastname: Li
mesh_terms: D002192:Canrenone / Q000737:chemistry*; D018360:Crystallography, X-Ray; D000077545:Eplerenone; D006801:Humans; D000451:Mineralocorticoid Receptor Antagonists / Q000138:chemical synthesis*; D015394:Molecular Structure; D013148:Spironolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000451:Mineralocorticoid Receptor Antagonists; D013148:Spironolactone; D000077545:Eplerenone; D002192:Canrenone