Collect. Czech. Chem. Commun. 2011, 76, 2023-2083
https://doi.org/10.1135/cccc2011099
Published online 2012-02-02 12:26:06

Recent developments in syntheses of the post-secodine indole alkaloids. Part III: Rearranged alkaloid types

Josef Hájíčeka,b

a Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030/8, 12840 Prague 2, Czech Republic
b Synthesis Development Group II, Zentiva, k.s., U kabelovny 130, 102 37 Prague 10, Czech Republic

This article is part of serial A Review on Recent Developments in Syntheses of the Post-Secodine Indole Alkaloids.

Abstract

The third part of a planned review on developments in the field of total and formal total synthesis of the post-secodine indole alkaloids focuses on types of rearranged alkaloids, i.e. on the skeletons with altered connectivities next to the indol(e)ine moiety, especially with a new bond to N-1. It reviews the synthesis of melodane, goniomitine, chippiine/dippinine, lirofoline and tronocarpine alkaloids, as well as alkaloids of secoschizozygane/vallesamidine, schizozygane and isoschizozygane type. It covers the literature from approximately 1991 up to May 2011. A review with 115 references.

Keywords: Indole alkaloids; Post-secodine alkaloids; Total synthesis; Asymmetric synthesis; Melodane alkaloids; Meloscine; Scandine; Goniomitine; Lirofoline; Chippiine/dippinine alkaloids; Tronocarpine; Secoschizozygane alkaloids; Schizozygane alkaloids; Isoschizozygane alkaloids; Vallesamidine; Strempeliopine; Schizozygine; Isoschizogamine.

References: 116 live references.