Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL.

Tozo FUJII; Masashi OHBA; Shigeki SETO

doi:10.1248/cpb.43.49

Quinolizidines. XXXIII. A Chiral Synthesis of (-)-Ophiorrhizine, a Pentacyclic Quaternary Indole Alkaloid from Ophiorrhiza major RIDL.

藤井澄三, 大場正志, 瀬戸茂樹

著者情報

キーワード: Ophiorrhiza alkaloid synthesis, ophiorrhizine configuration, cincholoipon, lactim ether N-alkylation, oxazolium hydrogenolysis, Bischler-Napieralski cyclization

ジャーナルフリー

1995 年 43 巻 1 号 p. 49-52

DOI https://doi.org/10.1248/cpb.43.49

詳細

抄録

A detailed account is given of the first chiral synthesis of the Ophiorrhiza alkaloid ophiorrhizine [(-)-1]. The synthesis was started by coupling the lactim ether (+)-4, readily available from cincholoipon ethyl ester [(+)-3], with 6-benzyloxy-3-chloroacetylindole (6) to form the lactam ketone (+)-8 and proceeded through the intermediates (+)-9, (+)-10, 11, (-)-12, (-)-13, 14, (-)-15, and (-)-16. The identity of synthetic (-)-1·H₂O with natural ophiorrhizine unequivocally established the absolute stereochemistry of this alkaloid.

責任著者(Corresponding author)

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