49. An Enantioselective Total Synthesis of Natural (+)-Luciduline
    Oppolzer, W.; Petrzilka, M.
    Helv. Chim. Acta 1978, 61, 2755-2762

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.

DOI : 10.1002/hlca.19780610802