Extreme Diels-Alder Reactions Your Chemistry Teacher Warned You About

🧠 Remember your chemistry introduction to Diels-Alder reactions? At that time, these extreme reactions would have been beyond your wildest imagination. If you want to learn some unique aspects to one of the most versatile and robust reactions known to chemists, check out this video! We will focus on two natural product total syntheses, covering basic organic chemistry and advanced synthesis.

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00:00 Exotic reactions hidden within complex structures
01:02 Natural product isolation basics | Biosynthetic origins of lissodendoric acid A and manzamine
04:58 Retrosynthesis of lissodendoric acid A | Allenes and Diels-Alder cycloaddition
08:37 Forward synthesis of lissodendoric acid A
12:06 ♡ Thank you for your support ♡
12:27 Context and retrosynthetic analysis of pedrolide
14:26 Caveat on cyclopentadienes in synthesis
16:27 Forward synthesis of pedrolide

Key references:
Lissodendoric Acids A and B, Manzamine-Related Alkaloids from the Far Eastern Sponge Lissodendoryx florida | Org. Lett. 2017, 19, 5320
Revisiting the manzamine biosynthetic hypothesis | Nat. Prod. Rep. 2023, 40, 964
Mercuric ion catalyzed rearrangements of ten-membered-ring allenes | J. Org. Chem. 1975, 40, 585
Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene | Science 2023, 379, 261
Diels–Alder cycloadditions of strained azacyclic allenes | Nat. Chem. 2018, 10, 953
Pedrolane, a Polycyclic Diterpene Scaffold Containing a Bicyclo[2.2.1]heptane System, from Euphorbia pedroi | Org. Lett. 2021, 23, 274
Enantioselective Total Synthesis of (+)-Pedrolide | J. Am. Chem. Soc. 2023, 145, 8332

Some recommended books on organic synthesis:
Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures)