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

Barcelona Institute of Science and Technology
Universitat Rovira i Virgili

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

70 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

Funding

We thank Agencia Estatal de Investigacioń (CTQ2016-75960-P MINECO/AEI/FEDER, UE), AEI-Severo Ochoa Excellence Accreditation 2014−2018 (SEV-2013-0319), the European Research Council (Advanced Grant no. 321066), the AGAUR (2014 SGR 818 and predoctoral fellowship to M.S.K.), and CERCA Program/Generalitat de Catalunya for financial support. M.E.M. acknowledges the receipt of a COFUND postdoctoral fellowship (Marie Skłodowska-Curie actions). We also thank the ICIQ X-ray diffraction unit for the crystallographic studies.

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b13484Licence: CC BY

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AU - Echavarren, Antonio M.

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

Abstract

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