Asymmetric synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles.
Hydrolysis of scalemic trichloroacetamides Cl(3)CCONHCH(R)CHCH(2) and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC(6)H(4)). Extension of this methodology with R = CH(2)CHCH(2) employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
Nomura
Hiroshi
H
School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, NR4 7TJ, UK.
Richards
Christopher J
CJ