Total Synthesis of Hunterine A

An organic chemistry minilecture on the 'Enantioselective Total Synthesis of (−)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy' by Elliot F. Hicks, Kengo Inoue, and Brian M. Stoltz*. It features an asymmetric Noyori Transfer Hydrogenation, an Aza-Cope Mannich reaction cascade and a creative triazoline photodecomposition.
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References:
J. Am. Chem. Soc. 2024, 146, 4340−4345 (This work)
J. Org. Chem. 2019, 84, 14892−14897. (Isolation)
Tetrahedron Lett. 1988, 29, 5413−5416 (Alkylation)
Chem. Scand. 1959, 13, 1943−1954 (Gilman Reaction Mechanism Review)
Tet. Lett. 1985, 26, 6015 (TMSCl as an additive in Gilman Reactions)
J. Am. Chem. Soc. 1993, 115, 20, 9283-9284 (TMSCl as an additive in Gilman Reactions)
Chem. Soc. Rev., 2000,29, 393-401 (TMSCl as an additive in Gilman Reactions)
Chem. Eur. J. 1999, 5, 9, 2680-2691 (TMSCl as an additive in Gilman Reactions)
J. Am. Chem. Soc. 1996, 118, 10, 2521-2522 (Noyori Transfer Hydrogenation)
J. Am. Chem. Soc. 2003, 125, 44, 13490-13503 (Noyori Transfer Hydrogenation)
Nature Reviews Chemistry 2018, 2, 396-408 (Noyori Transfer Hydrogenation)
Chem.Commun. 2003, 396−397 (Grignard)
J. Org. Chem.1989, 54, 1236−1238. (Aza-Cope Mannich Cascade)

[@dzhangarbadmaev1057]

Please don't stop doing what you're doing. Your effort is highly appreciated!

[@SamaelsWut]

Im working on a fairly complex polyketide myself but wouldn't have come up with that strategy in weeks of daily brainstorming. Highly condensed alkaloids are a treasure trove of genius ideas put to the test.

[@UniCorneliusfan21]

It’s always a good day when simplifying synthesis uploads

[@exuma7524]

Yay new Simplifying Synthesis vid

[@samirrezgui3680]

💯💯💯🔥🔥🔥

[@r9341-tss1]

I spent my masters degree working on a total synthesis. It didn't work, but it really has given me an appreciation for the work it needs. That cascade at the end was very elegant and I could only wish to see those disconnections.

[@user-tw1ui7zu1m]

At around