This Chemical Reaction Is Literal Magic & You Never Heard Of It

⚛️ If you need to brush up on quantum mechanics or other topics in science, math or programming, go to https://brilliant.org/TotalSynthesis/ to explore Brilliant for free for a full 30 days. You’ll also get 20% off an annual premium subscription. This video was sponsored by Brilliant. If there is a chemistry cheat code, this reaction might be it. In this video, we explain the theoretical grounds and practical applications of dyotropic reactions. In these rearrangements, two sigma bonds migrate simultaneously or "swap places". This first part will involve some time travel, discussion of the infamous Woodward-Hoffmann rules and discovery of strange paper footnotes. In the second part, we discover how these reactions facilitated a synthesis of a cancer-killing worm molecule - because why not. https://total-synthesis.com/organic-c... 🧑‍🎓➡️ Free organic chemistry practice problems   / totalsynthesis_official   👉 Follow me on Instagram for updates on random research, mechanism quizzes and interesting news! 00:00 Your teacher HATES this simple chemistry trick 01:27 PART 1: Steroids, fertile grounds for many chemistry insights 02:39 Dyotropic reaction mechanism, Manfred Reetz and type I dyotropic reactions 04:10 Entering the rabbit hole: Woodward-Hoffmann 05:14 Conservation of orbital symmetry, orbital diagrams and symmetry operations 07:02 Allowed reaction (Diels-Alder) and "forbidden" reaction ([2+2] addition) 09:35 How can you achieve your learning goals better and faster? 11:19 A shortcut to symmetry-allowed vs. symmetry-forbidden reactions 14:05 Exiting the rabbit hole: How do we categorize sigma-bond migrations? 15:31 Why do forbidden reactions occur? Secondary orbital effects 17:22 Type II dyotropic reactions, and visiting an old friend 19:02 Where to find free organic chemistry practice problems 19:18 Dyotropic reactions in nature 20:35 PART 2: 160kg of Cephalodiscus worms, and shark alarm 21:55 Structure-activity relationship in cephalostatins 23:25 Why we need total synthesis of natural products 25:17 Synthesis A: "Brute force" 26:10 Synthesis B: "Dyotropic elegance" 29:27 Many stories end without a happy end Key publications: PART 1: DYOTROPIC REACTIONS Angew. Chem. Int. Ed. 1972, 11, 129 | Dyotropic Rearrangements, a New Class of Orbital-Symmetry Controlled Reactions. Type I Tetrahedron 1973, 29, 2189 | Primary and secondary orbital effects in dyotropic rearrangements Angew. Chem. Int. Ed. 1969, 8, 781 | The Conservation of Orbital Symmetry Adv. Organomet. Chem. 1977, 16, 33 | Dyotropic Rearrangements and Related σ-σ Exchange Processes Helvetica Chimica Acta 1972, 55, 67 | The Stabilization of Bridged Structures of Ethanes Chem. Rev. 2009, 109, 6687 | Dyotropic Reactions: Mechanisms and Synthetic Applications Chem. Eur. J. 2006, 12, 6323 | Stereoelectronic Effects on Type I 1,2-Dyotropic Rearrangements in Vicinal Dibromides Angew. Chem. Int. Ed. 1972, 11, 130 | Dyotropic Rearrangements, a New Class of Orbital-Symmetry Controlled Reactions. Type II PART 2: CEPHALOSTATIN J. Am. Chem. Soc. 1988, 110, 2006 J. Nat. Prod. 2015, 78, 1446 J. Am. Chem. Soc. 1998, 120, 692 Chem. Rev. 2009, 109, 2275 J. Am. Chem. Soc. 2002, 124, 4548 Recommended organic chemistry books: Winter; Organic Chemistry I For Dummies (start here if you are absolutely friggin clueless) | https://amzn.to/4fmF97q Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge) | https://amzn.to/4ul57ft Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis) | https://amzn.to/4fmF97q | https://amzn.to/3Q529xn Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions) | https://amzn.to/43cbzKH Grossmann; The Art of Writing Reasonable Organic Reaction Mechanisms (building intuition for intermediate and advanced reaction mechanisms) | https://amzn.to/4dOiIXA Nicolaou; Classics in Total Synthesis 1-4 (simply legendary series) | https://amzn.to/4o986pz | https://amzn.to/3ROsRLp | https://amzn.to/3S4vCYV | https://amzn.to/4dPI9YL Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life) | https://amzn.to/4odZwWW Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures) | https://amzn.to/4dZk9kH Anslyn; Modern Physical Organic Chemistry (almost anything you will need for (organic) physical chemistry) | https://amzn.to/4gwOZUL