22282-00-4Relevant academic research and scientific papers
(endo, endo)-9-Benzyl-9-azabicyclo[3.3.1]nonane-2,6-diol: An intermediate for the preparation of indole alkaloids of the macroline/sarpagine series
Gennet, Dominique,Michel, Patrick,Rassat, Andre
, p. 447 - 451 (2007/10/03)
Two intermediates 9b and 9c already used by Cook and Magnus in their syntheses of indole alkaloids were obtained from the title compound 1 through a Fischer indolization procedure. Related tetracyclic intermediates 6 and 8 were also prepared: 6 having substituents at position 2 or 4 were directly obtained, while 8 with substituents at position 1 or 3 were selectively obtained through a convenient protection-deprotection scheme.
Pictet-Spengler reactions in aprotic media. The total synthesis of (±) suaveoline
Trudell,Soerens,Weber,Hutchins,Grubisha,Bennett,Cook
, p. 1805 - 1822 (2007/10/02)
The first total synthesis of the indole alkaloid (±)-suaveoline 1 (a macroline-related base and a member of the sarpagine/ajmaline class of alkaloids) was completed in a stereocontrolled fashion. The serial synthesis employed three intramolecular reaction
Selenium Dioxide Oxidations in the Indole Area. Synthesis of β-Carboline Alkaloids
Cain, M.,Campos, O.,Guzman, F.,Cook, J.M.
, p. 907 - 913 (2007/10/02)
A number of different piperidoindole systems have been subjected to oxidation with selenium dioxide.The bonding between the indole and piperidine unit has been varied to provide different systems, the oxidation of which has led to formation of either 2-acyl- or 3-acylindoles or fully aromatic β-carbolines, depending on the substrate chosen.The pattern of reactivity observed was in complete agreement with the ene mechanism proposed for selenium dioxide oxidations, and this can be employed to predict the regiochemistry of the oxidation.Use of this technology has resulted in a two-step synthesis of the indole alkaloid canthin-6-one (30a).
