An approach to the total synthesis of welwistatin.
An approach to the total synthesis of the antimicrotubule agent welwistatin is described. Key transformations include (1) a 7-endo intramolecular conjugate addition reaction of enone 6 to deliver the strained bicyclo[4.3.1]decanone 5; (2) a 6pi electrocyclic ring closure of trienecarbamate 16 followed by oxidation to afford protected aniline 17; and (3) an intramolecular cyclization of acetic acid derivative 18 to give rise to indole 19. [reaction: see text]
Greshock
Thomas J
TJ
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Funk
Raymond L
RL
D000470:Alkaloids / Q000138:chemical synthesis*; D000458:Cyanobacteria / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids; D008870:Microtubules / Q000187:drug effects; D015394:Molecular Structure
D000470:Alkaloids; D026121:Indole Alkaloids; C092270:welwitindolinone C isothiocyanate