Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Fedor M. Miloserdov; Mariia S. Kirillova; Michael E. Muratore; Antonio M. Echavarren

doi:10.1021/jacs.7b13484

Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Fedor M. Miloserdov, Mariia S. Kirillova, Michael E. Muratore, Antonio M. Echavarren

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

49 Citations (SciVal)

Abstract

The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8-endo-dig hydroarylation and a 6-exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided.

Original language	English
Pages (from-to)	5393-5400
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	140
Issue number	16
Early online date	12 Feb 2018
DOIs	https://doi.org/10.1021/jacs.7b13484
Publication status	Published - 25 Apr 2018

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b13484Licence: CC BY

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Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Abstract

ASJC Scopus subject areas

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