Abstract
AbstractThe reaction of the key compound 14 with methyl 4‐formyl‐butanoate (9) or with 5‐benzoyloxypentanal (13) gave the D‐seco‐aspidospermane derivatives 17 and 18, respectively. Compound 17 was indirectly and 18 was directly converted to (±)‐20‐deethylvincadifformine (7) and (±)‐20‐deethyl‐20‐epivincadifformine (8). Epimerization occurred in both cases. The thioxo compound 23 was used for the synthesis of (±)‐20‐deethyltabersonine (28) and (±)‐20‐deethyl‐3‐oxotabersonine (27). Oxidative ring transformation of the (±)‐20‐deethylvincadifformine (7) gave (±)‐16‐deethylapovincamine (29).
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