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The naturally occurring Lycopodium alkaloid (+)‐luciduline (1) has been synthesized from (R)‐5‐methyl‐cyclohex‐2‐en‐1‐one (12) by a sequence of seven steps (s. Scheme 6) in 33% overall yield. The key step 4→6 presumably involves a transient nitrone 5 which undergoes a highly regioselective intramolecular addition to a non‐polarized olefinic bond.
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Oppolzer et al. (1978) studied this question.
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