(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester

(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester 화학적 특성, 용도, 생산

• 개요

  This alkaloid which has been obtained from the leaves of Pleiocarpa talbotii Wernham contains a secondary N(b) atom and a cyclic hemiacetal group. It is strongly laevorotatory having [α]>_D - 200° (CHC13). A secondary hydroxyl group is present and the base forms an O-methyl ether, m.p. 155-6°C. The O,N-diacetyl derivative is also crystalline with m.p. 190-3°C. Catalytic hydrogena_x0002_tion leads to 19: 2D-dihydrota1botine. When treated with NaOMe and NaOH the alkaloid yields two products, a lactone and a hydroxymethy1 compound in which the hemiacetal ring is opened. These data, together with the infrared and NMR spectra, lead to the complete relative stereochemistry of the alkaloid.

• 참고 문헌

  Pinar et al., Helv. Chim. Acta, 54, 15 (1971)