A new total synthesis of (–)-suaveoline from L-tryptophan is reported (overall yield ca. 14%); key steps include a high yielding cis-specific Pictet–Spengler reaction, a one-pot Horner–Wadsworth–Emmons/alkylation procedure, a vinylogous Thorpe cyclization and the direct formation of a pyridine from a 1,5-dinitrile.
P. D. Bailey and K. M. Morgan, Chem. Commun., 1996, 1479 DOI: 10.1039/CC9960001479
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