23665-97-6Relevant articles and documents
Total synthesis of rhodonoids a, b, e, and f, enabled by singlet oxygen ene reactions
Burchill, Laura,George, Jonathan H.
, p. 2260 - 2265 (2020)
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.
A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols
Luo, Guo-Ying,Wu, Hao,Tang, Yu,Li, Hui,Yeom, Hyun-Suk,Yang, Ka,Hsung, Richard P.
, p. 2713 - 2720 (2015/09/15)
Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation-oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.
