Total synthesis of (±)-aspidospermidine, (±)-aspidofractinine, (±)-limaspermidine, and (±)-vincadifformine via a cascade and common intermediate strategy
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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.
Cain , D , Anderson , N , Cordes , D B , Slawin , A M Z & Watson , A J B 2022 , ' Total synthesis of (±)-aspidospermidine, (±)-aspidofractinine, (±)-limaspermidine, and (±)-vincadifformine via a cascade and common intermediate strategy ' , The Journal of Organic Chemistry , vol. 87 , no. 22 , pp. 15559–15563 . https://doi.org/10.1021/acs.joc.2c02099
The Journal of Organic Chemistry
Copyright © 2022 The Authors. Published by American Chemical Society. This article is distributed under the terms of the Creative Commons Attribution 4.0 License (https://creativecommons.org/licenses/by/4.0/) which permits any use, reproduction and distribution of the work without further permission provided the original work is correctly attributed.
DescriptionFunding: D.L.C. thanks EPSRC and GSK for a Ph.D. studentship.
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