The first asymmetric synthesis of phenanthroquinolizidinealkaloid (R)‐boehmeriasin A is described. Two alternative synthetic pathways to the key intermediate (RS,R)‐4 were achieved through a combination of highly diastereoselective 1,2‐nucleophilic addition on (–)‐(S)‐1‐amino‐2‐(methoxymethyl)pyrrolidine hydrazones with a ring‐closing metathesis to ensure the construction of the piperidine template. A subsequent acylation/oxidation/aldol condensation/radical cyclization sequence completed the assembly of the title (R)‐configured natural product.
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Dumoulin et al. (2010) studied this question.
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