55 THE TOTAL SYNTHESIS OF COCCINELLINE AND PRECOCCINELLINE

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概要

• 論文の詳細を見る

• Precoccinelline and the corresponding N-oxide coccinelline are defensive substances secreted by certain members of the family Coccinellidae (polka-dot beetles or ladybugs). The synthesis of these alkaloids is described. The starting material is 2,6-lutidine which was first alkylated on the 2-methyl group with (β-bromopropionaldehyde acetal then acetylated on the 6-methyl group. Reduction of the protected ketoaldehyde with sodium-isoamyl alcohol gave predominantly the cis-2,6-piperidine derivative which afforded a mixture of two tricyclic ketones when cyclized using pyrrolidine and acetic acid. The appropriate tricyclic ketone was transformed in three steps to precoccinelline. Oxidation of precoccinilline gave coccinelline. The unusual isomerization of the cis-2,6-piperidine derivative during the cyclization step is discussed.

• 天然有機化合物討論会の論文
• 1976-09-20

著者

• Ayer William

  Department Of Chemistry University Of Alberta

• Furuichi Kimiaki

  Department Of Chemistry Graduate School Of Science Osaka City University

• Furuichi Kimiaki

  Department Of Chemistry University Of Alberta:(present Office)department Of Chemistry Faculty Of Sci

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• 55 THE TOTAL SYNTHESIS OF COCCINELLINE AND PRECOCCINELLINE

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