The first total synthesis of resveratrone and iso-resveratrone based on an epoxide olefination approach is described. The pivotal reaction proceeds by insertion of the lithiated epoxide into a boronic ester and subsequent syn-elimination. Resveratrone has been described to have remarkable photophysical properties, including two-photon absorption. Therefore, an azide derivative has been prepared to allow for use as a biological label.
Keywords: epoxide; fluorescence label; olefination; resveratrone; total synthesis.
© 2022 The Authors. Published by Wiley-VCH GmbH.