<jats:title>Abstract</jats:title><jats:p>Two novel tropolone derivatives <jats:bold>1</jats:bold> and <jats:bold>2</jats:bold> have been isolated from <jats:italic>Goupia glabra</jats:italic>. Their structures were determined by extensive 1D and 2D NMR spectroscopic studies. Compound <jats:bold>2</jats:bold> constitutes the first example isolated from a natural source of a Diels−Alder adduct between a tropolone and a naphthalene derivative. Compounds <jats:bold>1</jats:bold> and <jats:bold>2</jats:bold> exhibit significant toxicity towards a panel of DNA damage checkpoint defective yeast mutants, and behave as genotoxins, which highlights their potential to be used as anticancer drugs. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)