Total Synthesis of (+)-Cochlearol B

An organic chemistry minilecture on the Total Synthesis of ( )-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2 2] Cycloaddition by Alistair D. Richardson, Trenton R. Vogel, Emily F. Traficante, Kason J. Glover, and Corinna *. Highlights include a Kabbe Condensation, an enaminone to unsaturated aldehyde transformation and an unusual Grignard deprotection of a methyl ether SUPPORT THE CHANNEL ON PATREON: NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 Socials: References: Angew. Chem. Int. Ed. 2022, e202201213 (This work) Org. Lett. 2014, 16, 6064–6067 (Isolation) Angew. Chem. Int. Ed. 2021, 60, 24484–24487 (Previous synthesis) Angew. Chem. Int. Ed. Engl. 1982, 21, 247-256 (Kabbe Condensation) J. Am. Chem. Soc. 1997, 119, 9913-9914 (Sulphinamide Chiral Resolution) Nat. Chem. 2019, 11, 1106-1112 (Catellani Reaction) J. Am. Chem. Soc. 2016, 138, 9269–9276 (Catellani Reaction) Nature. 2017, 551, 489 (Catellani Reaction) Angew. Chem. Int. Ed. 2012, 51, 1–5 (Photo cycloaddition) Chem. Rev. 2016, 116,9748–9815 (Photo cycloaddition) Angew. Chem., Int. Ed. 2012, 51, 10329−10332 (Photo cycloaddition) J. Org. Chem. 2021, 86, 7333−7346 (DMF-DMA Enaminone Formation) Mini-Reviews in Organic Chemistry 2020; 17(1) (Bredericks Reagent Review) Chem. Ber. 1968, 101, 41 (Bredericks Reagent)