title: The first regiospecific, enantiospecific total synthesis of 6-oxoalstophylline and an improved total synthesis of alstonerine and alstophylline as well as the bisindole alkaloid macralstonine.
abstract: A Wacker sequence has been modified to rapidly generate ring E of (-)-alstonerine, (+)-6-oxoalstophylline, and (-)-alstophylline via a domino process. This one-pot sequence provides facile entry into the dihydropyranyl enone unit of many Alstonia alkaloids. [structure: see text]
authors.affiliation: Department of Chemistry, University of Wisconsin-Milwaukee, 3210 North Cramer Street, Milwaukee, WI 53211, USA.
authors.forename: Xuebin
authors.initials: X
authors.lastname: Liao
authors.forename: Hao
authors.initials: H
authors.lastname: Zhou
authors.forename: Xiangyu Z
authors.initials: XZ
authors.lastname: Wearing
authors.forename: Jun
authors.initials: J
authors.lastname: Ma
authors.forename: James M
authors.initials: JM
authors.lastname: Cook
mesh_terms: D031051:Alstonia / Q000737:chemistry*; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds; D013237:Stereoisomerism
chemical_list: C510441:6-oxoalstophylline; D026121:Indole Alkaloids; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C510442:alstonerine; C510443:alstophylline; C467067:macralstonidine