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

David Cain, Niall Anderson, David B. Cordes, Alexandra M. Z. Slawin, Allan J. B. Watson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

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.
Original languageEnglish
Pages (from-to)15559–15563
Number of pages5
JournalThe Journal of Organic Chemistry
Volume87
Issue number22
Early online date19 Oct 2022
DOIs
Publication statusPublished - 18 Nov 2022

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