Stereorational total synthesis of (.+-.)-porantherine

DM Ryckman, RV Stevens

Index: Ryckman,D.M.; Stevens,R.V. Journal of the American Chemical Society, 1987 ,  vol. 109, p. 4940            

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Citation Number: 19

Abstract

Abstract: An efficient stereorational total synthesis of (f)-porantherine (l), the major alkaloid isolated from Poranthera corymbosa, is described. The synthesis features two stereospecific Mannich-type condensations. Novel dialkylpiperidine 20 is prepared by the addition of 2 equiv of 5-lithio-2-pentanone 2', 2'-dimethylpropylene ketal (19) to 0-methylvalerolactim. Porantherine is obtained in 31% overall yield.