Formation of benzo[b]fluorenes and the benzo[a]fluorene core of the fluostatins by cyclization of diaryldiynones

Abstract

[figure: see text] Thermal cyclization of 1-[2-(trimethylsilylethynyl)phenyl]-3-arylpropinones was expected to give benzo[b]fluorenones. However, benzo[a]-fluorenones were also formed as a result of a new rearrangement. These tetracycles possess the core structure of the fluostatins and isoprekinamycin.