Synthesis of the 1‑Phenethyltetrahydroisoquinoline
Alkaloids (+)-Dysoxyline, (+)-Colchiethanamine, and (+)-Colchiethine
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Abstract
Asymmetric total syntheses of the 1-phenethyl-1,2,3,4-tetrahydroisoquinoline
alkaloids (+)-dysoxyline (<b>1</b>), (+)-colchiethanamine (<b>2</b>), and (+)-colchiethine (<b>3</b>) are described. In
the synthetic routes, coupling of a key, enatiomerically pure 1-(sulfonylmethyl)tetrahydroisoquinoline
with aromatic aldehydes, performed by using the Julia–Kocienski
reaction, afforded the corresponding 1-(β-styryl)-substituted
tetrahydroisoquinolines with complete retention of the absolute configuration
at the C1 carbon atom. Functionalization of the products generated
in these processes by using four- or five-step sequences gave the
target alkaloids <b>1</b>–<b>3</b>