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Literature DB >> 18069843

First total synthesis of trimeric indole alkaloid, psychotrimine.

Yohei Matsuda¹, Mariko Kitajima, Hiromitsu Takayama.

Abstract

The first total synthesis of (+/-)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved. In the total synthesis, the copper-mediated intramolecular and intermolecular aminations of halobenzenes, which respectively contributed to the construction of a pyrrolidinoindoline core and the installation of a third tryptamine unit, were used as key steps.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 18069843 DOI： 10.1021/ol702637r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

19 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors: Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal: J Am Chem Soc Date: 2010-05-26 Impact factor: 15.419

3. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors: Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

4. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors: Stephen P Lathrop; Mohammad Movassaghi
Journal: Chem Sci Date: 2014-01-01 Impact factor: 9.825

First total synthesis of trimeric indole alkaloid, psychotrimine.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

3. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

4. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Review 5. Protecting-group-free synthesis as an opportunity for invention.

6. Why do some Fischer indolizations fail?

7. Concise Total Synthesis of (+)-Gliocladins B and C.

8. Chemoselectivity: the mother of invention in total synthesis.

9. Concise Total Synthesis of (+)-Luteoalbusins A and B.

10. Concise Total Synthesis of (+)-Bionectins A and C.