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

Chemical Science
Anna E SalvatiJames H Frederich

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.

References

Feb 28, 2003·The EMBO Journal·Martin WürteleClaudia Oecking
Aug 2, 2003·Nature Reviews. Cancer·Gordon B Mills, Wouter H Moolenaar
Aug 8, 2008·Organic Letters·Lei LiF G West
Oct 7, 2009·Proceedings of the National Academy of Sciences of the United States of America·G V SubbaraoO Ito
Mar 23, 2010·Current Opinion in Chemical Biology·Matthew E WelschBrent R Stockwell
Mar 30, 2010·Chemistry, an Asian Journal·Feng HuangZhi-Xiang Yu
Sep 15, 2011·Angewandte Chemie·Kazuhiro TsunaMasahisa Nakada
Apr 3, 2012·Trends in Plant Science·Albertus H de Boer, Ingrid J de Vries-van Leeuwen
Dec 28, 2012·Proceedings of the National Academy of Sciences of the United States of America·Malgorzata SkwarczynskaChristian Ottmann
May 17, 2013·Proceedings of the National Academy of Sciences of the United States of America·Ingrid J De Vries-van LeeuwenAlbertus H de Boer
Mar 18, 2015·Chemical Reviews·Daisuke UrabeMasayuki Inoue

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Citations

Nov 7, 2019·Angewandte Chemie·Danny Q ThachThomas J Maimone
Apr 20, 2021·Angewandte Chemie·James A LawJames H Frederich
Apr 25, 2020·Organic Letters·Hui ShaoYong-Qiang Tu

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Methods Mentioned

BETA
NMR
X-ray

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