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.
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]
Liao
Xuebin
X
Department of Chemistry, University of Wisconsin-Milwaukee, 3210 North Cramer Street, Milwaukee, WI 53211, USA.
Zhou
Hao
H
Wearing
Xiangyu Z
XZ
Ma
Jun
J
Cook
James M
JM
D031051:Alstonia / Q000737:chemistry*; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds; D013237:Stereoisomerism
C510441:6-oxoalstophylline; D026121:Indole Alkaloids; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C510442:alstonerine; C510443:alstophylline; C467067:macralstonidine