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Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides†
Wei Sun,Surajit Kayal,William A. T. Raimbach,Xue-Zhong Sun,Mark E. Light,Magnus W. D. Hanson-Heine,David C. Harrowven
Chemical Communications Pub Date : 12/23/2021 00:00:00 , DOI:10.1039/D1CC06800H
Abstract

Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heterocycles show the value of the methods, while TA-spectroscopy and TD-DFT studies provide mechanistic insights on their wavelength dependence.

Graphical abstract: Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides
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