Total Synthesis of Aspidosperma and Strychnos Alkaloids through Indole Dearomatization

Jordy M Saya; Eelco Ruijter; Romano V A Orru

doi:10.1002/chem.201901130

Total Synthesis of Aspidosperma and Strychnos Alkaloids through Indole Dearomatization

Chemistry. 2019 Jul 5;25(38):8916-8935. doi: 10.1002/chem.201901130. Epub 2019 May 16.

Authors

Jordy M Saya¹, Eelco Ruijter¹, Romano V A Orru¹

Affiliation

¹ Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems, Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ, Amsterdam, The Netherlands.

PMID: 30994212
DOI: 10.1002/chem.201901130

Abstract

Monoterpenoid indole alkaloids are the major class of tryptamine-derived alkaloids found in nature. Together with their structural complexity, this has attracted great interest from synthetic organic chemists. In this Review, the syntheses of Aspidosperma and Strychnos alkaloids through dearomatization of indoles are discussed.

Keywords: alkaloids; biomimetic synthesis; dearomatization; indoles; natural product synthesis.

Publication types

Review

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Aspidosperma / chemistry*
Chemistry Techniques, Synthetic / methods*
Cycloaddition Reaction / methods
Secologanin Tryptamine Alkaloids / chemical synthesis
Secologanin Tryptamine Alkaloids / chemistry
Strychnos / chemistry*

Substances

Alkaloids
Secologanin Tryptamine Alkaloids

Grants and funding

n.a./NWO