Total Synthesis of Rhodonoids A, B, E, and F, Enabled by Singlet Oxygen Ene Reactions
Laura Burchill, Jonathan H. George
Abstract
Singlet oxygen is a versatile reagent for the selective oxidation of organic compounds under mild reaction conditions. It is frequently invoked in biosynthetic pathways, so it is especially suitable for application in the biomimetic synthesis of natural products. Herein, we show that use of the singlet oxygen ene reaction, combined with [2 + 2] cycloadditions, leads to concise, divergent, and redox-economic total syntheses of several polycyclic members of the rhodonoid family of meroterpenoids.
Topics & Concepts
Singlet oxygenEne reactionChemistryReagentRedoxOxygenSinglet statePhotochemistryCombinatorial chemistryOrganic chemistryExcited statePhysicsNuclear physicsMarine Sponges and Natural ProductsPhytochemistry and Bioactivity StudiesPhytochemistry and Biological Activities