Enantioselective total synthesis of (-)-dehydrobatzelladine C. [structure: see text].
The oxidation of two tethered Biginelli adducts was examined as a potential key step in total syntheses of highly oxidized batzelladine and crambescidin alkaloids. Although angular hydroxyl substitution could not be introduced, dehydrogenation was readily accomplished. This latter conversion is a key step in the first total synthesis of dehydrobatzelladine C. [structure: see text]
Collins
Shawn K
SK
Department of Chemistry, 516 Rowland Hall, University of California at Irvine, Irvine, CA 96697-2025, USA.
McDonald
Andrew I
AI
Overman
Larry E
LE
Rhee
Young Ho
YH
D000470:Alkaloids / Q000138:chemical synthesis*; D006146:Guanidines / Q000138:chemical synthesis*; D006865:Hydrogenation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000470:Alkaloids; D006146:Guanidines; C496159:dehydrobatzelladine C