Enantiospecific, stereospecific total synthesis of the oxindole alkaloid alstonisine.
[reaction: see text] The total synthesis of alstonisine was accomplished in enantiospecific fashion in an overall yield of 12% (from tryptophan methyl ester) in 17 reaction vessels. The structure of alstonisine (1) has been determined by NOE spectroscopic experiments and was confirmed by single-crystal X-ray analysis.
Wearing
Xiangyu Z
XZ
Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
Cook
James M
JM
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D031051:Alstonia / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds; D013237:Stereoisomerism
D000470:Alkaloids; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C470641:alstonisine