Quinolizidines. XIX. Synthesis of (-) -9-Demethyltubulosine

TOZO FUJII; MASASHI OHBA; HIROSHI HATAKEYAMA

doi:10.1248/cpb.35.2355

TOZO FUJII, MASASHI OHBA, HIROSHI HATAKEYAMA

著者情報

キーワード: Alangium vitiense alkaloid, demethyltubulosine, chiral synthesis, demethylisotubulosine, diethyl phosphorocyanidate amide formation, Bischler-Napieralski cyclization, carbon-nitrogen double-bond catalytic reduction, benzyl ether hydrogenolysis, CD epimer differentiation

ジャーナルフリー

1987 年 35 巻 6 号 p. 2355-2359

DOI https://doi.org/10.1248/cpb.35.2355

詳細

抄録

The chirál synthesis of (-) -9-demethyltubulosine [(-) -1] has been achieved for the first time via a “cincholoipon-incorporating route, ” which started from cincholoipon ethyl ester [(+) -7] and passed through the intermediates (-) -8, (-) -9, (+) -10, and (+) -11. As a result, the absolute configuration of the Alangium vitiense alkaloid 9-demethyltubulosine has been unequivocally established to be that represented by formula (-) -1.

責任著者(Corresponding author)

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