This Surprising Synthesis Will Teach You Organic Chemistry (Rauvomine B)

🤯 "Protecting groups protect" - Makes sense, right? Well, until it doesn't. In this video, we will learn more about this, and explore interesting organic chemistry reactions by studying the total synthesis of rauvomine B (note: not peer reviewed yet so it could be all made up).

  / totalsynthesis  
🚀 Thanks to all channel supporters!!!
  / totalsynthesis_official  
👉 Follow me on IG to learn about interesting news and mechanism quizzes!
https://www.total-synthesis.com

00:00 Surprises with protecting groups
00:38 Rauvolfia natural products
02:16 Retrosynthesis of rauvomine B
03:42 Forward synthesis: CBS reduction/ kinetic resolution, allylation
05:57 Allylation deep dive
08:21 Pictet-Spengler, selenoxide elimination, ring closing metathesis (RCM)
10:39 Pivotal step: Cycloaddition, Rhodium-catalyzed cyclopropanation, hydrolysis
11:42 The effect of the Boc protecting group
14:50 Conclusion and outlook

Key references:
- 10.26434/chemrxiv-2024-jp63v-v2 | Total Synthesis of (–)-Rauvomine B via a Strain-Promoted Intramolecular Cyclopropanation (Preprint)
- Org Lett 2017, 19, 3998 | Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria
- JACS 1992, 114, 6858 | Isomerization of (pi-allyl)palladium complexes via nucleophilic displacement by palladium(0). A common mechanism in palladium(0)-catalyzed allylic substitution
- Org. Lett. 2019, 21, 8473 | Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin