☆ 4.8 Article

Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

ORGANIC LETTERS (2009)

期刊

ORGANIC LETTERS

卷 11, 期 13, 页码 2892-2895

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AMER CHEMICAL SOC

DOI: 10.1021/ol900880w

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Chemistry, Organic

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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-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

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