Synthesis of a protected trihydroxyindolizidine 3-carboxylate via a hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to a D-ribose-derived exo-glycal.
A protected trihydroxyindolizidine 3-carboxylate was prepared by a 6-endo epoxide cleavage, which in turn was intermediately formed from the hetero-Diels-Alder adduct of ethyl 2-nitrosoacrylate to a D-ribose-derived exo-glycal.
Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece.
Zoe S
ZS
Massen
Evdoxia
E
Coutouli-Argyropoulou
Vassiliki C
VC
Sarli
John K
JK
Gallos
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D054836:Indolizidines / Q000138:chemical synthesis*; D009574:Nitro Compounds; D009603:Nitroso Compounds / Q000138:chemical synthesis*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D012266:Ribose / Q000737:chemistry*
D000179:Acrylates; D004852:Epoxy Compounds; D054836:Indolizidines; D009574:Nitro Compounds; D009603:Nitroso Compounds; D011763:Pyrrolizidine Alkaloids; D012266:Ribose; C036658:acrylic acid