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Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy
[Image: see text] 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 cas...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680024/ https://www.ncbi.nlm.nih.gov/pubmed/36259765 http://dx.doi.org/10.1021/acs.joc.2c02099 |
| _version_ | 1784834318827257856 |
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| author | Cain, David L. Anderson, Niall A. Cordes, David B. Slawin, Alexandra M. Z. Watson, Allan J. B. |
| author_facet | Cain, David L. Anderson, Niall A. Cordes, David B. Slawin, Alexandra M. Z. Watson, Allan J. B. |
| author_sort | Cain, David L. |
| collection | PubMed |
| description | [Image: see text] 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. |
| format | Online Article Text |
| id | pubmed-9680024 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-96800242022-11-23 Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy Cain, David L. Anderson, Niall A. Cordes, David B. Slawin, Alexandra M. Z. Watson, Allan J. B. J Org Chem [Image: see text] 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. American Chemical Society 2022-10-19 2022-11-18 /pmc/articles/PMC9680024/ /pubmed/36259765 http://dx.doi.org/10.1021/acs.joc.2c02099 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Cain, David L. Anderson, Niall A. Cordes, David B. Slawin, Alexandra M. Z. Watson, Allan J. B. Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy |
| title | Total Synthesis
of (±)-Aspidospermidine,
(±)-Aspidofractinine,
(±)-Limaspermidine, and (±)-Vincadifformine via a Cascade
and Common Intermediate Strategy |
| title_full | Total Synthesis
of (±)-Aspidospermidine,
(±)-Aspidofractinine,
(±)-Limaspermidine, and (±)-Vincadifformine via a Cascade
and Common Intermediate Strategy |
| title_fullStr | Total Synthesis
of (±)-Aspidospermidine,
(±)-Aspidofractinine,
(±)-Limaspermidine, and (±)-Vincadifformine via a Cascade
and Common Intermediate Strategy |
| title_full_unstemmed | Total Synthesis
of (±)-Aspidospermidine,
(±)-Aspidofractinine,
(±)-Limaspermidine, and (±)-Vincadifformine via a Cascade
and Common Intermediate Strategy |
| title_short | Total Synthesis
of (±)-Aspidospermidine,
(±)-Aspidofractinine,
(±)-Limaspermidine, and (±)-Vincadifformine via a Cascade
and Common Intermediate Strategy |
| title_sort | total synthesis
of (±)-aspidospermidine,
(±)-aspidofractinine,
(±)-limaspermidine, and (±)-vincadifformine via a cascade
and common intermediate strategy |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680024/ https://www.ncbi.nlm.nih.gov/pubmed/36259765 http://dx.doi.org/10.1021/acs.joc.2c02099 |
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