The Journal of organic chemistry

Synthesis of the pentacyclic skeleton of the aspidosperma alkaloids using rhodium carbenoids as reactive intermediates

A Padwa, AT Price

Index: Padwa, Albert; Price, Alan T. Journal of Organic Chemistry, 1998 , vol. 63, # 3 p. 556 - 565

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Citation Number: 104

Abstract

A series of diazo amido keto esters prepared from N-alkenyl-substituted 3-carbalkoxy-2- piperidone derivatives was treated with rhodium (II) acetate. Attack of the amido carbonyl oxygen at the resultant rhodium carbenoid center produced a transient push-pull carbonyl ylide dipole which underwent an intramolecular dipolar cycloaddition reaction. A related annulation sequence was used to prepare the pentacyclic skeleton of the aspidosperma ...