Highly stereoselective total syntheses of indole alkaloids vindorosine (la) and vindoline (lb) are described.An imino Diels-Alder reaction, a stereospecific alkylation, and a rearrangement induced by the Pummerer reaction are the key steps of these short and high overall yield sequences.Aspidosperma alkaloid vindoline (lb)2 is with catharanthine (2a)3 the direct biogenetic precursor4 of the an-titumor alkaloids of Catharanthus roseus like vinblastine (3).5 The discovery in our laboratory6 of a hemisynthetic
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