## Abstract Die erste Totalsynthese des racemischen Alkaloids Pumiliotoxin‐C (9) ausgehend von __trans__‐1‐Brom‐3‐penten (1) wird beschrieben. Die Schlüsselstufe 6 → 7 verläuft über eine intramolekulare __Diels__‐__Alder__‐Reaktion unter weitgehender sterischer Kontrolle von vier Chiralitätszentren
Total Synthesis of (±)-Pumiliotoxin C: An Electrochemical Approach
✍ Scribed by Nicolas Girard; Jean-Pierre Hurvois; Claude Moinet; Loic Toupet
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 202 KB
- Volume
- 2005
- Category
- Article
- ISSN
- 1434-193X
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📜 SIMILAR VOLUMES
The convergent total synthesis of pumiliotoxins by attachment of the side chain to a suitably functionalized core indolizidinone derivative has been achieved. The use of an aldoltype addition condensation strategy, intended to provide for the stereoselective generation of the exocyclic double bond,
A method is described for the synthesis of pumiliotoxin C acrylates was transformed into bromide using the tosylate method. Cyclization of the bromides led to unsaturated (1a) and related stereoisomeric compounds 1c-1f. Starting from (+)-or (-)-3-methylcyclohexanone (6a,b), the oxo esters quinoline