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Year 2005, Month 9 (Section Brief Communications, Page 2229)

Synthesis of 8,9-(1,3-benzodioxolo-5,6)- 5-azatricyclo[8.2.1.01,5]tridec-11-en-6-one. A convenient route to structural analogs of the alkaloid cephalotaxine*

N. Yu. Kuznetsov, I. V. Zhun´, V. N. Khrustalev, and Yu. N. Bubnov*

A synthetic route to 8,9-(1,3-benzodioxolo-5,6)-5-azatricyclo[8.2.1.01,5]tridec-11-en-6- one structurally isomeric to the pentacyclic cephalotaxine nucleus is suggested. The route is based on the sequence including diallylboration of 2-pyrrolidinone and intramolecular meta- thesis of the resulting 2,2-diallylpyrrolidine, giving rise to 1-azaspiro[4.4]non-7-ene. This product was N-acylated with 6-bromohomopiperonylic acid chloride and then subjected to intramolecular cyclization according to the Heck reaction.

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