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

58 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

Access to Document

10.1021/jacs.7b13484Licence: CC BY

Cite this

@article{fc4220d9edc04806870d49b3c1a22914,

title = "Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship",

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.",

author = "Miloserdov, {Fedor M.} and Kirillova, {Mariia S.} and Muratore, {Michael E.} and Echavarren, {Antonio M.}",

year = "2018",

month = apr,

day = "25",

doi = "10.1021/jacs.7b13484",

language = "English",

volume = "140",

pages = "5393--5400",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

AU - Miloserdov, Fedor M.

AU - Kirillova, Mariia S.

AU - Muratore, Michael E.

AU - Echavarren, Antonio M.

PY - 2018/4/25

Y1 - 2018/4/25

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85045973049&partnerID=8YFLogxK

U2 - 10.1021/jacs.7b13484

DO - 10.1021/jacs.7b13484

M3 - Article

C2 - 29432680

AN - SCOPUS:85045973049

SN - 0002-7863

VL - 140

SP - 5393

EP - 5400

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 16

ER -

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

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this