Asymmetric synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles

Hiroshi Nomura, Christopher J. Richards

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Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 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-MeOC6H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
Original languageEnglish
Pages (from-to)2892-2895
Number of pages4
JournalOrganic Letters
Issue number13
Publication statusPublished - 29 May 2009

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