Total synthesis of (±)-aspidospermidine, (±)-aspidofractinine, (±)-limaspermidine, and (±)-vincadifformine via a cascade and common intermediate strategy

Autor: David L. Cain, Niall A. Anderson, David B. Cordes, Alexandra M. Z. Slawin, Allan J. B. Watson
Přispěvatelé: University of St Andrews. School of Chemistry, University of St Andrews. EaSTCHEM, University of St Andrews. Sir James Mackenzie Institute for Early Diagnosis
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Popis: Funding: D.L.C. thanks EPSRC and GSK for a Ph.D. studentship. A concise strategy for the total synthesis of several Aspidosperma alkaloids is reported. A Suzuki–Miyaura cross-coupling provides access to a 2-vinyl indole that undergoes a Diels–Alder cascade reaction with butyn-2-one to deliver a pyrroloindoline intermediate. This undergoes cascade amidation, reduction, skeletal rearrangement, and intramolecular Michael addition to provide a common intermediate containing the full framework of the Aspidosperma alkaloids. The utility of this intermediate is shown in the synthesis of four different natural products. Publisher PDF
Databáze: OpenAIRE