✍ Scribed by Alexander Sudau; Winfried Münch; Jan-W. Bats; Udo Nubbemeyer
No coin nor oath required. For personal study only.
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, gave no satisfactory results. The method of choice was a Horner olefination. Initially, the reactant core indolizidinone was converted into an α phosphono amide by amide enolate formation, enol phosphate generation, and a final phosphatephosphonate migration. The amido phosponates smoothly [ ‡] Introduction of the Side Chain, 2. Part 1: Ref. [11] [a]
📜 SIMILAR VOLUMES
## 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