Utilization of protopine and related alkaloids. XIV. Oxidation of the photoadduct of 1-oxoanhydromethylberberine with nitrosobenzene, and synthesis of ring C-substituted benzo(c)phenanthridines.

DOI Web Site

抄録

Oxidation of the photo-adduct (2) with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone under anhydrous conditions gives the imine (3) and the aniline (4). The oxidation of 2 in the presence of water and anhydrous methanol affords the 1-oxo-2β, 4β-epoxyimine (6) and the 4bα-methoxy-10bβ, 12β-epoxyimine (8), respectively. The mechanisms of formation of these compounds are discussed. The quinone (5), derived from 3 and 4, is reduced with sodium borohydride to yield the cis-diol (25) and the trans-diol (26). On reduction with lithium aluminum hydride and subsequent hydrogenation over palladiumcarbon, 8 gives the 4bβH-12β-anilino-10bβ-ol (33) and the 4bαH isomer (34).

収録刊行物

キーワード

詳細情報 詳細情報について

問題の指摘

ページトップへ