New approach to the stereocontrolled total synthesis of peridinin-5, 8-furanoxides

摘要

In 2003, Iguchi and co-workers isolated two C37-norcarotenoids, structurally related to peridinin 1, from a symbiont dinoflagellate symbiodinimium sp. of the Okinawan soft coral Clavularia viridis. The structure of these two compounds, which was assigned using different NMR techniques, IR and MS-spectrometry feature an allene group, an γ-alkylidenebutenolide and five hydroxylated stereocenters. They were identified as diastereomeric at C-8 on the dihydrofuran ring and named all-trans-(8R,6R)-peridinin-5,8-furanoxide 2 and all-trans-(8S,6R)-peridinin-5,8-furanoxide 3.