Total synthesis of (-)- and ent-(+)-vindoline.
[reaction: see text] Two exceptionally concise total syntheses of (-)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C-C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.
Choi
Younggi
Y
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Ishikawa
Hayato
H
Velcicky
Juraj
J
Elliott
Gregory I
GI
Miller
Michael M
MM
Boger
Dale L
DL
D001688:Biological Products / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001688:Biological Products; C009667:vindoline; D014747:Vinblastine