604-99-9Relevant articles and documents
Stereospecific total synthesis of the indole alkaloid ervincidine. Establishment of the C-6 hydroxyl stereochemistry
Rallapalli, Sundari K.,Namjoshi, Ojas A.,Tiruveedhula, V. V. N. Phani Babu,Deschamps, Jeffrey R.,Cook, James M.
supporting information, p. 3776 - 3780 (2014/05/20)
The total synthesis of the indole alkaloid ervincidine (3) is reported. This research provides a general entry into C-6 hydroxy-substituted indole alkaloids with either an α or a β configuration. This study corrects the errors in Glasby's book (Glasby, J. S. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975) and Lounasmaa et al.'s review (Lounasmaa, M.; Hanhinen, P.; Westersund, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1999; Vol. 52, pp 103-195) as well as clarifies the work of Yunusov et al. (Malikov, V. M.; Sharipov, M. R.; Yunusov, S. Yu. Khim. Prir. Soedin. 1972, 8, 760-761. Rakhimov, D. A.; Sharipov, M. R.; Aripov, Kh. N.; Malikov, V. M.; Shakirov, T. T.; Yunusov, S. Yu. Khim. Prir. Soedin. 1970, 6, 724-725). It establishes the correct absolute configuration of the C-6 hydroxyl function in ervincidine. This serves as a structure proof and corrects the misassigned structure reported in the literature.
General approach for the total synthesis of the sarpagine related indole alkaloids (+)-Na-methyl-16-epipericyclivine, (-)-alkaloid Q3 and (-)-panarine via the asymmetric Pictet-Spengler reaction
Yu, Jianming,Wearing, Xiangyu Z.,Cook, James M.
, p. 543 - 547 (2007/10/03)
The stereospecific total synthesis of (+)-Na-methyl-16-epipericyclivine (1) was completed [from D-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels). The optical rotation {[α]D +22.8 (c 0.50, CHCl3
General approach for the synthesis of sarpagine/macroline indole alkaloids. Enantiospecific total synthesis of the indole alkaloid trinervine.
Liu,Cook
, p. 4023 - 4026 (2007/10/03)
[structure: see text] The total synthesis of the indole alkaloid trinervine 1 was accomplished in enantiospecific fashion in an overall yield of 20% (from the tetracyclic ketone 8) in 10 reaction vessels (12.5% from tryptophan methyl ester). The synthesis of the N(a)-H substituted macroline equivalent 2 was also completed in high yield via the same intermediate 13. The unique protection/hydroboration process developed here should provide a method to functionalize the C(19)-C(20) double bond in similar systems.
