防己科植物アルカロイド研究 (第147報)

ミヤコジマツヅラフジCyclea insularis (MAKINO) DIELSのアルカロイド その11 Cyclanolineの構造 (2)

抄録

Positions of the two phenolic hydroxyls in cyclanoline were examined. Permanganate oxidation of O, O-diethylcyclanoline afforded 5-ethoxy-4-methoxyphthalic acid (I), 3-ethoxy-4-methoxyphthalic acid (II), and 7-ethoxy-6-methoxy-1-oxo-1, 2, 3, 4-tetrahydroisoquinoline (IV). It was found that the N-demethyl compound derived from O, O-diethylcyclanoline iodide was identical with l-O, O-diethylscoulerine, and therefore, cyclanoline was proved to be l-α-N-methylscoulerine (V).