Department of Chemistry, Center for Molecular Discovery (BU-CMD), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts, 02215, USA.
Present address: Department of Chemistry and Center for Photochemical Sciences, Bowling Geen State University, Bowling Green, OH, 43403, USA.
Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14479-14482. doi: 10.1002/anie.201707539. Epub 2017 Oct 13.
Selective excited-state intramolecular proton-transfer (ESIPT) photocycloaddition of 3-hydroxyflavones with trans, trans-1,4-diphenyl-1,3-butadiene is described. Using this methodology, total syntheses of the natural products (±)-foveoglin A and (±)-perviridisin B were accomplished. Enantioselective ESIPT photocycloaddition using TADDOLs as chiral hydrogen-bonding additives provided access to (+)-foveoglin A. Mechanistic studies have revealed the possibility for a photoinduced electron-transfer (PET) pathway.
本文描述了 3-羟基黄酮与反式, 反式-1,4-二苯基-1,3-丁二烯的选择性激发态分子内质子转移(ESIPT)光环加成反应。利用这种方法,完成了天然产物(±)-foveoglin A 和(±)-perviridisin B 的全合成。使用 TADDOL 作为手性氢键添加剂的对映选择性 ESIPT 光环加成反应为(+)-foveoglin A 的获得提供了途径。机理研究揭示了光诱导电子转移(PET)途径的可能性。