Total synthesis of (+/-)-welwitindolinone a isonitrile.
A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.
Reisman
Sarah E
SE
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Ready
Joseph M
JM
Hasuoka
Atsushi
A
Smith
Catherine J
CJ
Wood
John L
JL
D000458:Cyanobacteria / Q000737:chemistry; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry
D026121:Indole Alkaloids; D007211:Indoles; D009570:Nitriles; C507638:welwitindolinone A