Biomimetic synthesis and structural revision of (+/-)-tridachiahydropyrone

Organic Letters
Pallavi SharmaJohn E Moses

Abstract

A short synthesis of the revised structure of the marine natural product tridachiahydropyrone is described. A novel biomimetic photochemical electrocyclization was employed to construct the bicyclic carbon framework from an open-chain polyene precursor. The spectroscopic data matched that of the isolated natural product, supporting a revised structure of this complex metabolite.

References

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Jul 27, 2004·Proceedings of the National Academy of Sciences of the United States of America·Aubry K MillerDirk Trauner
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Mar 26, 2005·Chemical Communications : Chem Comm·John E MosesJack E Baldwin
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Citations

Sep 20, 2016·Organic Letters·Zhiqiang RenXiangdong Hu
Aug 30, 2017·Natural Product Reports·Patrick D Brown, Andrew L Lawrence
May 18, 2018·Natural Product Research·Rohani Prasad BurmanManjinder Singh Gill
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Jul 2, 2010·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep
Jan 20, 2011·Angewandte Chemie·Thorsten Bach, Jörg P Hehn
Oct 4, 2012·Physical Chemistry Chemical Physics : PCCP·Kimberley J PowellPaul O'Shea
Apr 4, 2009·Journal of the American Chemical Society·Pallavi SharmaJohn E Moses

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