Hydride-Induced Rearrangements with Indole Alkaloid Intermediates

Hydride-Induced Rearrangements with Indole Alkaloid Intermediates 

During studies on the total synthesis of Aspidosperma type alkaloids, unexpected difficulty was encountered in attempts to reduce the amide carbonyl group of the intermediate 1. Thus, many attempts to reduce 1 with lithium aluminium hydride resulted in reduction of both the amide carbonyl group and the C=C double bond. In an effort to circumvent this problem 1 was reacted with hot phosphorus oxychloride and the intermediate thus obtained treated with sodium borohydride in anhydrous methanol. The product which was isolated, however, was the pentacyclic compound 2, which was obtained in 50% yield. 

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