Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry

[Image: see text] 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 ( J. S. GlasbyEncyclopedia of the Alka...

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Autores principales: Rallapalli, Sundari K., Namjoshi, Ojas A., Tiruveedhula, V. V. N. Phani Babu, Deschamps, Jeffrey R., Cook, James M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4017614/
https://www.ncbi.nlm.nih.gov/pubmed/24697213
http://dx.doi.org/10.1021/jo402692u
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author Rallapalli, Sundari K.
Namjoshi, Ojas A.
Tiruveedhula, V. V. N. Phani Babu
Deschamps, Jeffrey R.
Cook, James M.
author_facet Rallapalli, Sundari K.
Namjoshi, Ojas A.
Tiruveedhula, V. V. N. Phani Babu
Deschamps, Jeffrey R.
Cook, James M.
author_sort Rallapalli, Sundari K.
collection PubMed
description [Image: see text] 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 ( J. S. GlasbyEncyclopedia of the Alkaloids; Plenum Press: New York, 1975) and Lounasmaa et al.’s review ( M. Lounasmaa; P. Hanhinen; M. Westersund In The Alkaloids; G. A. Cordell, Ed.; Academic Press: San Diego, CA, 1999; Vol. 52, pp 103–195) as well as clarifies the work of Yunusov et al. ( V. M. Malikov; M. R. Sharipov; S. Yu. YunusovKhim. Prir. Soedin.1972, 8, 760−761. D. A. Rakhimov; M. R. Sharipov; Kh. N. Aripov; V. M. Malikov; T. T. Shakirov; S. Yu. YunusovKhim. 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.
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spelling pubmed-40176142015-04-03 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. J Org Chem [Image: see text] 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 ( J. S. GlasbyEncyclopedia of the Alkaloids; Plenum Press: New York, 1975) and Lounasmaa et al.’s review ( M. Lounasmaa; P. Hanhinen; M. Westersund In The Alkaloids; G. A. Cordell, Ed.; Academic Press: San Diego, CA, 1999; Vol. 52, pp 103–195) as well as clarifies the work of Yunusov et al. ( V. M. Malikov; M. R. Sharipov; S. Yu. YunusovKhim. Prir. Soedin.1972, 8, 760−761. D. A. Rakhimov; M. R. Sharipov; Kh. N. Aripov; V. M. Malikov; T. T. Shakirov; S. Yu. YunusovKhim. 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. American Chemical Society 2014-04-03 2014-05-02 /pmc/articles/PMC4017614/ /pubmed/24697213 http://dx.doi.org/10.1021/jo402692u Text en Copyright © 2014 American Chemical Society
spellingShingle Rallapalli, Sundari K.
Namjoshi, Ojas A.
Tiruveedhula, V. V. N. Phani Babu
Deschamps, Jeffrey R.
Cook, James M.
Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry
title Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry
title_full Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry
title_fullStr Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry
title_full_unstemmed Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry
title_short Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry
title_sort stereospecific total synthesis of the indole alkaloid ervincidine. establishment of the c-6 hydroxyl stereochemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4017614/
https://www.ncbi.nlm.nih.gov/pubmed/24697213
http://dx.doi.org/10.1021/jo402692u
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