Atisines

Athletes foot Athletic surfaces Atisine Ativan ATJ graphite Atmosphere... 

This C2Q pyrophosphate (122), thought to provide the carbon framework of the diterpene alkaloids such as veatchine (123), atisine (124),... 

A. hakusanense, Nakai (Japan). Aconitine, hypaconitine, mesaconitine. A. heterophyllum.. Wall. Atisine (p. 687). 

Craig in a critical revision of previous work. Atisine is a colourless... 

Both Lawson and Topps and Jacobs and Craig have investigated the dehydrogenation of atisine by selenium. The results are not imme-... 

A. heterophyllum, in which atisine was the chief alkaloid, after standing four years, yielded 8 grams of isoatisine, due to isomerisation with heter-atisine. O 4 gm., and atisine hydrochloride, 0-35 gm. ... 

Jacobs and Craig found two other alkaloids in the mother liquors accumulated during the isolation of atisine from A. heterophyllum. 

Hexahydrobenzoyloxodedelphonine acetate (VI) was dehydrogenated by selenium at 330° and gave as chief product a hydrocarbon, b.p. 90°/0-02 mm., whose composition, ultra-violet absorption spectrum and chemical properties, so far as examined, indicate that it may be a bicyclopentenobenzene and therefore in a different category from the phenanthrene hydrocarbons yielded by the atisine group of bases. 

The C2o-diterpene alkaloids have long served as classic targets within the field of natural product synthesis [14], Total syntheses of four C2o-diterpene alkaloids have thus far been reported atisine [15], veatchine [16], garryine [17], and napelline [18]. In spite of this progress, synthetic efforts toward the hetisine alkaloids have been relatively sparse. Prior to our work in the area, these efforts include one total synthesis and five synthetic studies. 

Treatment of the ketone (105) with methanolic KOH led to hydrolysis of the acetate group, retro-aldol reaction and aldol cyclization, which eventually afforded a mixture of epimeric alcohols (106) 33). This strategy was used to construct the basic skeletons of various alkaloids, e.g. talatisamine 34), atisine 35) and chasmanine36). 

Dr. Ken ichi Takeda, then Director of Shionogi Research Laboratories, Na-gata extended his research efforts to include the first total synthesis of the diterpene alkaloid group including atisine, garryine, and veatchine as well as the gibberellins all in their racemic form. 

The isomerization of atisine to isoatisine and the conformational analysis of rings E and F of atisine, veatchine, and related alkaloids have been studied by n.m.r. spectroscopy. 12-O-Acetylnapelline is a new alkaloid which has been isolated from Aconitum karakolicum. 

The lactam (Formula 470) has been converted to Formula 471 which proved to be the enantiomer of a degradation product of atisine (209). This clarifies the stereochemistry of the atisine alkaloids, the garrya alkaloids, and related diterpenes (209). 

MW 299.2249 Atisine-/V,20-azomethine Azitine Cuauchichicine-N,20-azome thine Garryfoline-/V,20-azomethine Veatchine-N,20-azome thine C20H29NO... 

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