A highly conjunctive beta-keto phosphonate: application to the synthesis of pyridine alkaloids xestamines C, E, and H.
The synthesis of a novel beta-keto gamma-xanthyl phosphonate has been achieved. This highly conjunctive reagent has been utilized in a combination of radical and ionic reactions to create new carbon-carbon bonds. Its usefulness was demonstrated by realizing the first total synthesis of naturally occurring pyridine alkaloids xestamines C, E, and H.
Corbet
Matthieu
M
Laboratoire de Synthèse Organique, CNRS UMR 7652, Département de Chimie, Ecole Polytechnique, 91128 Palaiseau, France.
de Greef
Michiel
M
Zard
Samir Z
SZ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D063065:Organophosphonates; D011725:Pyridines; C526632:xestamine C; C526633:xestamine E; C526634:xestamine H