title: One-pot organocatalytic enantioselective Michael-Michael-aldol-Henry reaction cascade. A facile entry to the steroid system with six contiguous stereogenic centers.
abstract: An expedited method has been developed for the enantioselective synthesis of highly functionalized steroid systems containing six contiguous stereogenic centers with high enantioselectivities (99% ee). The one-pot methodology comprises a cascade of organocatalytic Michael-Michael-aldol-Henry reactions of 7-nitrohept-3-en-2-one and 5-(1-methyl-2,5-dioxocyclopentyl)pent-2-enal. The structure and absolute configuration of the products were confirmed by X-ray analyses of appropriate products.
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi, 621, Taiwan R.O.C.
authors.forename: Dai-Huei
authors.initials: DH
authors.lastname: Jhuo
authors.forename: Bor-Cherng
authors.initials: BC
authors.lastname: Hong
authors.forename: Chun-Wei
authors.initials: CW
authors.lastname: Chang
authors.forename: Gene-Hsiang
authors.initials: GH
authors.lastname: Lee
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D013256:Steroids; C064599:2-pentenal; C116609:3-hydroxybutanal