Total Synthesis of Resiniferatoxin Enabled by Photocatalytic Decarboxylative Radical Cyclization
Yuto Hikone, Takehiro Kato, Masanori Nagatomo, Masayuki Inoue
Abstract
that requires 27 steps from a starting d-ribose derivative. The carbon spacer and A-ring are sequentially attached to the C-ring by radical allylation and Stille coupling reactions, respectively. An Ir(III)-catalyzed photoinduced decarboxylative radical reaction then forged the sterically hindered bond between the tetra- and trisubstituted carbons to cyclize the central seven-membered B-ring.
Topics & Concepts
ChemistryResiniferatoxinRing (chemistry)Radical cyclizationStille reactionTotal synthesisStannaneDerivative (finance)Steric effectsStereochemistryMedicinal chemistryPhotochemistryCombinatorial chemistryCatalysisOrganic chemistryTransient receptor potential channelReceptorFinancial economicsBiochemistryTRPV1EconomicsBioactive Natural Diterpenoids ResearchPlant-based Medicinal ResearchBiological Activity of Diterpenoids and Biflavonoids