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Synthesis of Bisbenzannulated SpiroketalsModel Studies for a Modular Approach to Rubromycins

2006; American Chemical Society; Volume: 8; Issue: 21 Linguagem: Inglês

10.1021/ol061932w

1523-7060

Sebastian Sörgel, Cengiz Azap, Hans‐Ulrich Reißig,

Synthesis and Biological Activity

A highly flexible synthesis of bisbenzannulated spiroketals is described with additions of lithiated methoxyallene to aryl aldehydes and Heck reactions as key steps. Subsequent hydrogenations and ketalizations afforded the desired spiroketals in good yields and with predominating trans-configuration. With model compound 30, already bearing the fully substituted naphthyl core of rubromycins, the ketalization proceeded efficiently providing the expected product 31 and the isopropoxy compound 32. Both products are advanced model compounds of heliquinomycin.