Allocolchicinoid Synthesis Via Direct Arylation

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2005 Jul 1

PMID 15987152

Citations 15

Authors

Melissa Leblanc

Keith Fagnou

Affiliations

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Abstract

[reaction: see text] A formal enantioselective synthesis of allocolchicine and a synthesis of a C-ring analogue have been achieved by employing an intramolecular direct arylation of an aryl chloride to form the biaryl carbon-carbon bond and the seven-membered ring.

Citing Articles

Electrooxidative tricyclic 6-7-6 fused-system domino assembly to allocolchicines by a removable radical strategy.

Zhang Y, Ma C, Cai Z, Struwe J, Chen S, Xu J Green Chem. 2022; 24(9):3697-3703.

PMID: 35694222 PMC: 9086860. DOI: 10.1039/d2gc00684g.

Dibenzocycloheptanones construction through a removable -centered radical: synthesis of allocolchicine analogues.

Zhang Y, Cai Z, Struwe J, Ma C, Zeng W, Liao X Chem Sci. 2022; 12(47):15727-15732.

PMID: 35003604 PMC: 8654019. DOI: 10.1039/d1sc05404j.

Formal Synthesis of (±)-Allocolchicine Via Gold-Catalysed Direct Arylation: Implication of Aryl Iodine(III) Oxidant in Catalyst Deactivation Pathways.

Corrie T, Lloyd-Jones G Top Catal. 2020; 60(8):570-579.

PMID: 32025176 PMC: 6979697. DOI: 10.1007/s11244-017-0742-z.

Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Campeau L, Hazari N Organometallics. 2019; 38(1):3-35.

PMID: 31741548 PMC: 6860378. DOI: 10.1021/acs.organomet.8b00720.

Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization.

Paymode D, Ramana C ACS Omega. 2019; 2(9):5591-5600.

PMID: 31457824 PMC: 6644368. DOI: 10.1021/acsomega.7b00980.