Total Synthesis of Lissodendoric Acid A

An organic chemistry minilecture on the ’Total Synthesis of Lissodendoric Acid A Via Stereospecific Trapping of a Strained Cyclic Allene’ by Francesca M. Ippoliti, Nathan J. Adamson, Laura G. Wonilowicz, Daniel J. Nasrallah, Evan R. Darzi, Joyann S. Donaldson, Neil K. Garg*. It features a remarkably selective allene cycloaddition to build the azadecalin core, allowing for a ring closing metathesis reaction to form the macrocycle and selective reduction to complete the synthesis. ERRATUM: Pd shown for the first step of the Suzuki Coupling should be a Pd(0) complex. SUPPORT THE CHANNEL ON PATREON: NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 Socials: References: Science 2023,379, 261–265 (This work) J. Org. , 56, 6494–6496 (Conjugate addition of Zr reagent) Angew. Chem. Int. Ed., 1998, 37, 1986-2012 (CBS Reduction) Adv. Synth. Catal. 2012, 354, 813–817 (Silylation) Angew. Chem. Int. Ed. 2021,60, 14989–14997 (Studies on allene cycloaddition) J. Org. Chem. 1987, 52, 5048–5051 (Allylic Oxidation) Org. Lett. 2008, 10, 2, 289–292 (Conjugate reduction) Tetrahedron 70, 7593–7597 (2014). (Cu Boc Deprotection) Chem. Eur. J. 2016, 22, 7050 – 7053 (Amide Reduction)