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Synfacts 2011(7): 0723-0723  
DOI: 10.1055/s-0030-1260619
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Lightning Quick Photoclick

Contributor(s): Timothy M. Swager, Olesya Haze
S. Arumugam, V. V. Popik*
University of Georgia, Athens, USA
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

The power of photodehydration of 3-(hydroxymethyl)-2-naphthols (1) and subsequent hetero-Diels-Alder cycloaddition of the ­resulting 2-naphthoquino-3-methides (2) with electron-rich polarized alkenes (3) is combined to produce a versatile ligation platform. Appropriately substituted vinyl ethers and enamines yield photostable benzochromans (4), incorporating permanent (green and blue) and/or acid-labile (red) linkages.