Bromination–dehydrobromination of saturated 1,6-dioxaspiro[4.4]nonanes afforded a variety of naturally occurring 1,6-dioxaspiro[4.4]-nonenes and -nonadienes, such as 2–5 and 8, and can be applied to give unsaturated spirolactones, such as 27.
Y. Q. Tu, K. A. Byriel, C. H. L. Kennard and W. Kitching, J. Chem. Soc., Perkin Trans. 1, 1995, 1309 DOI: 10.1039/P19950001309
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