Synthesis of (±)-Lysergic Acid

An organic chemistry minilecture on the 'Six-Step Synthesis of (±)-Lysergic Acid' by Brian J. Knight, Ryan C. Harbit, and Joel M. Smith*. It demonstrates a short, modular synthesis that can be used to synthesize analogues of LSD using a reductive dearomatization and an intramolecular Heck reaction.

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References:
J. Org. Chem. 2023, 88, 2158−2165 (This work)
Alex Grey-Albert Hofmann and the New Eleusis (A Hofman painting)
Angew. Chem.,Int. Ed. 2004, 43, 3333−3336 (Turbo Grignard)
Chem. Eur. J. 2019, 25, 2695−2703 (Turbo Grignard)
J. Am. Chem. Soc. 2001, 123, 29, 6989–7000 (Fu‘s Pd Complex)

0:00 Introduction
0:15 Six-Step Synthesis of (+)-Lysergic Acid
0:53 Strategy
1:25 Grignard Addition
1:41 Benzylic Reduction
2:09 Reductive Dearomatization
3:45 B-Hydride Elimination
4:30 Deprotection/ Isomerization
4:58 12-Chlorolysergic Acid