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Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation. [Reaction: see text]

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Total Synthesis of Natural (−)- and ent-(+)-4-Desacetoxy-6,7-dihydrovindorosine and Natural and ent-Minovine: Oxadiazole Tandem Intramolecular Diels−Alder/1,3-Dipolar Cycloaddition Reaction