Issue 24, 2018

Modular access to functionalized 5–8–5 fused ring systems via a photoinduced cycloisomerization reaction

Abstract

A 5–8–5 carbocyclic ring system forms the core of over 30 distinct natural products. Several members of this family have gained attention for their diverse activity in cell culture. In these cases, biological function is mediated by the arrangement of substituents around a conserved 5–8–5 nucleus. Despite the potential applications of this privileged substructure in medicinal chemistry, modular strategies for its assembly are underdeveloped. Herein, we describe a cycloisomerization reaction that forms the 5–8–5 framework directly. This strategy uniquely allows access to gram quantities of this valuable scaffold in four steps.

Graphical abstract: Modular access to functionalized 5–8–5 fused ring systems via a photoinduced cycloisomerization reaction

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Mar 2018
Accepted
22 May 2018
First published
25 May 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 5389-5393

Modular access to functionalized 5–8–5 fused ring systems via a photoinduced cycloisomerization reaction

A. E. Salvati, J. A. Law, J. Liriano and J. H. Frederich, Chem. Sci., 2018, 9, 5389 DOI: 10.1039/C8SC00999F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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