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Total Synthesis of Resiniferatoxin Enabled by Photocatalytic Decarboxylative Radical Cyclization.

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Resiniferatoxin (1) is a complex daphnane diterpenoid with a highly oxygenated 5/7/6-membered ABC-ring system. Here we report a new synthetic route to 1 that requires 27 steps from a starting… Click to show full abstract

Resiniferatoxin (1) is a complex daphnane diterpenoid with a highly oxygenated 5/7/6-membered ABC-ring system. Here we report a new synthetic route to 1 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.

Keywords: resiniferatoxin; synthesis resiniferatoxin; resiniferatoxin enabled; decarboxylative radical; enabled photocatalytic; total synthesis

Journal Title: Organic letters
Year Published: 2022

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