First Total Synthesis of (±)-Prelunularin

Abstract

The first total synthesis of (±)-prelunularin is described employing an intramolecular aldol addition/sulfinate elimination tandem reaction. Investigations on the mechanism of the one-pot cyclization reaction using time-dependent NMR spectroscopy suggested that the sulfinate elimination took place before the intramolecular ring-closing aldol addition.

tandem reactions - natural products - intramolecular cyclization

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