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)
1 view
1482
585
2 months ago 00:01:13 1
Red Alert 2 CG Opening Cinematic Reforged
2 months ago 00:35:43 20
Origin Overview - Our BIGGEST and BEST cinematic pack is HERE!
2 months ago 00:02:58 51
Origin - Cinematic Opus Magnum
2 months ago 00:28:10 1
Epic First Cocaine Synthesis in 25 Steps (Educational)