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dc.contributor.authorCain, David
dc.contributor.authorAnderson, Niall
dc.contributor.authorCordes, David B.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorWatson, Allan J. B.
dc.identifier.citationCain , 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 .
dc.identifier.otherPURE: 281688643
dc.identifier.otherPURE UUID: 7fa075c0-f873-425e-840c-ed4c8e546d02
dc.identifier.otherORCID: /0000-0002-9527-6418/work/121753932
dc.identifier.otherORCID: /0000-0002-5366-9168/work/121753994
dc.identifier.otherORCID: /0000-0002-1582-4286/work/121754394
dc.identifier.otherScopus: 85140639402
dc.identifier.otherWOS: 000876696900001
dc.descriptionFunding: D.L.C. thanks EPSRC and GSK for a Ph.D. studentship.en
dc.description.abstractA 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.
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.rightsCopyright © 2022 The Authors. Published by American Chemical Society. This article is distributed under the terms of the Creative Commons Attribution 4.0 License ( which permits any use, reproduction and distribution of the work without further permission provided the original work is correctly attributed.en
dc.subjectQD Chemistryen
dc.titleTotal synthesis of (±)-aspidospermidine, (±)-aspidofractinine, (±)-limaspermidine, and (±)-vincadifformine via a cascade and common intermediate strategyen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Sir James Mackenzie Institute for Early Diagnosisen
dc.description.statusPeer revieweden

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