Total synthesis of (±)-aspidospermidine, (±)-aspidofractinine, (±)-limaspermidine, and (±)-vincadifformine via a cascade and common intermediate strategy
Date
18/11/2022Metadata
Show full item recordAbstract
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.
Citation
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
Publication
The Journal of Organic Chemistry
Status
Peer reviewed
ISSN
0022-3263Type
Journal article
Description
Funding: D.L.C. thanks EPSRC and GSK for a Ph.D. studentship.Collections
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