Protecting-group directed stereoselective intramolecular nozaki-hiyamaKishi reaction: A concise and efficient total synthesis of amphidinolactone A

摘要

A convergent; total synthesis of amphidinolactone A, a cytotoxic macrolide from, the cultured dinoflagellate Amphidinium. sp., is described in 13 linear steps. The key step in the synthetic sequence involves an intramolecular NozakiHiyama-Kishi (NHK) reaction for the construction of the 13-membered lactone ring by union of two fragments derived from a single chiral epoxide. The stereochemical outcome of the NHK reaction has been supported by computational studies.