H. Nomura, C. Richards
May 29, 2009
Citations
0
Influential Citations
30
Citations
Journal
Organic letters
Abstract
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.