Saxitoxin: CIA Chemical Weapons, Biochemistry and Total Synthesis (Kishi, Jacobi, Du Bois)

Rindfleisch
Published on May 11, 2021
This video deals with the history and use of the marine natural product saxitoxin as a chemical weapon, its biochemistry and most importantly, strategies towards its total synthesis.

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00:00 Some comments on what I've been up to
00:58 History of saxitoxin and it's use in CIA operations
02:34 Medicinal background saxitoxin (paralytic shellfish poisoning, PSP) and short overview of mechanism of action (sodium channel blocker)
05:39 Retrosynthesis and strategy employed by Yoshito Kishi in 1977: Oldschool organic chemistry and electrocyclizations
07:42 Retrosynthesis and strategy employed by Peter Jacobi in 1984: Dipolar azomethine ylide cycloadditions and radical chemistry
09:37 Retrosynthesis and strategy employed by Du Bois in 2006:
Modern C-H functionalization and oxidations

References:
Kishi: https://pubs.acs.org/doi/abs/10.1021/ja00450a079
Jacobi: https://pubs.acs.org/doi/abs/10.1021/ja00331a032
Du Bois: https://pubs.acs.org/doi/abs/10.1021/ja071501o

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 reactions and applications thereof with common conditions)
- Nicolaou et al; 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)