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Molecules 2016, 21(11), 1525; doi:10.3390/molecules21111525

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53201, USA
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Author to whom correspondence should be addressed.
Academic Editor: Michael Wink
Received: 29 September 2016 / Revised: 30 October 2016 / Accepted: 4 November 2016 / Published: 14 November 2016
(This article belongs to the Special Issue Diversity of Alkaloids)

Abstract

Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthesis of bisindole alkaloids isolated primarily from the Alstonia genus of the Apocynaceae family. The monomeric units belong to the sarpagine, ajmaline, macroline, vobasine, and pleiocarpamine series. An up-to-date discussion of their isolation, characterization, biological activity as well as approaches to their partial and total synthesis by means of both synthetic and biosynthetic strategies are presented. View Full-Text
Keywords: Alstonia genus; Apocynaceae family; sarpagine; macroline; ajmaline; bisindole alkaloids; biomimetic synthesis; partial and total synthesis; enantiospecific and regiospecific synthesis of alkaloids; bioactive indole alkaloids Alstonia genus; Apocynaceae family; sarpagine; macroline; ajmaline; bisindole alkaloids; biomimetic synthesis; partial and total synthesis; enantiospecific and regiospecific synthesis of alkaloids; bioactive indole alkaloids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Rahman, M.T.; Tiruveedhula, V.V.N.P.B.; Cook, J.M. Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review. Molecules 2016, 21, 1525.

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