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A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
A full account of our studies toward reverse-prenylated indole alkaloids that contain a bicyclo[2.2.2]core is described. A divergent route is reported which has resulted in the synthesis of preparaherquamide, (+)-VM-55599, and premalbrancheamide. An intramolecular Dieckmann cyclization between an en...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7480500/ https://www.ncbi.nlm.nih.gov/pubmed/32953008 http://dx.doi.org/10.1039/d0sc02296a |
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author | Roque, Jose B. Mercado-Marin, Eduardo V. Richter, Sven C. Pereira de Sant'Ana, Danilo Mukai, Ken Ye, Yingda Sarpong, Richmond |
author_facet | Roque, Jose B. Mercado-Marin, Eduardo V. Richter, Sven C. Pereira de Sant'Ana, Danilo Mukai, Ken Ye, Yingda Sarpong, Richmond |
author_sort | Roque, Jose B. |
collection | PubMed |
description | A full account of our studies toward reverse-prenylated indole alkaloids that contain a bicyclo[2.2.2]core is described. A divergent route is reported which has resulted in the synthesis of preparaherquamide, (+)-VM-55599, and premalbrancheamide. An intramolecular Dieckmann cyclization between an enolate and isocyanate was used to forge the bicyclo[2.2.2]diazaoctane core that is characteristic of these molecules. The pentacyclic indole scaffold was constructed through a one-pot Hofmann rearrangement followed by Fischer indole synthesis. The utilization of our previously reported indole peripheral functionalization strategy also led to natural products including malbrancheamides B, C, stephacidin A, notoamides F, I and R, aspergamide B, and waikialoid A. Ultimately, the divergent route that we devised provided access to a wide range of prenylated indole alkaloids that are differently substituted on the cyclic amine core. |
format | Online Article Text |
id | pubmed-7480500 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-74805002020-09-18 A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599 Roque, Jose B. Mercado-Marin, Eduardo V. Richter, Sven C. Pereira de Sant'Ana, Danilo Mukai, Ken Ye, Yingda Sarpong, Richmond Chem Sci Chemistry A full account of our studies toward reverse-prenylated indole alkaloids that contain a bicyclo[2.2.2]core is described. A divergent route is reported which has resulted in the synthesis of preparaherquamide, (+)-VM-55599, and premalbrancheamide. An intramolecular Dieckmann cyclization between an enolate and isocyanate was used to forge the bicyclo[2.2.2]diazaoctane core that is characteristic of these molecules. The pentacyclic indole scaffold was constructed through a one-pot Hofmann rearrangement followed by Fischer indole synthesis. The utilization of our previously reported indole peripheral functionalization strategy also led to natural products including malbrancheamides B, C, stephacidin A, notoamides F, I and R, aspergamide B, and waikialoid A. Ultimately, the divergent route that we devised provided access to a wide range of prenylated indole alkaloids that are differently substituted on the cyclic amine core. Royal Society of Chemistry 2020-05-28 /pmc/articles/PMC7480500/ /pubmed/32953008 http://dx.doi.org/10.1039/d0sc02296a Text en This journal is © The Royal Society of Chemistry 2020 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Roque, Jose B. Mercado-Marin, Eduardo V. Richter, Sven C. Pereira de Sant'Ana, Danilo Mukai, Ken Ye, Yingda Sarpong, Richmond A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599 |
title | A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
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title_full | A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
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title_fullStr | A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
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title_full_unstemmed | A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
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title_short | A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
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title_sort | unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-vm-55599 |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7480500/ https://www.ncbi.nlm.nih.gov/pubmed/32953008 http://dx.doi.org/10.1039/d0sc02296a |
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