Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I

A unified strategy for the synthesis of congeners of the prenylated indole alkaloids is presented. This strategy has yielded the first synthesis of the natural product (–)-17-hydroxy-citrinalin B as well as syntheses of (+)-stephacidin A and (+)-notoamide I. An enolate addition to an in situ generat...

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Detalles Bibliográficos
Autores principales: Mercado-Marin, Eduardo V., Sarpong, Richmond
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4583210/
https://www.ncbi.nlm.nih.gov/pubmed/26417428
http://dx.doi.org/10.1039/c5sc01977j
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author Mercado-Marin, Eduardo V.
Sarpong, Richmond
author_facet Mercado-Marin, Eduardo V.
Sarpong, Richmond
author_sort Mercado-Marin, Eduardo V.
collection PubMed
description A unified strategy for the synthesis of congeners of the prenylated indole alkaloids is presented. This strategy has yielded the first synthesis of the natural product (–)-17-hydroxy-citrinalin B as well as syntheses of (+)-stephacidin A and (+)-notoamide I. An enolate addition to an in situ generated isocyanate was utilized in forging a key bicyclo[2.2.2]diazaoctane moiety, and in this way connected the two structural classes of the prenylated indole alkaloids through synthesis.
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spelling pubmed-45832102016-08-01 Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I Mercado-Marin, Eduardo V. Sarpong, Richmond Chem Sci Chemistry A unified strategy for the synthesis of congeners of the prenylated indole alkaloids is presented. This strategy has yielded the first synthesis of the natural product (–)-17-hydroxy-citrinalin B as well as syntheses of (+)-stephacidin A and (+)-notoamide I. An enolate addition to an in situ generated isocyanate was utilized in forging a key bicyclo[2.2.2]diazaoctane moiety, and in this way connected the two structural classes of the prenylated indole alkaloids through synthesis. Royal Society of Chemistry 2015-08-01 2015-06-18 /pmc/articles/PMC4583210/ /pubmed/26417428 http://dx.doi.org/10.1039/c5sc01977j Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Mercado-Marin, Eduardo V.
Sarpong, Richmond
Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I
title Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I
title_full Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I
title_fullStr Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I
title_full_unstemmed Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I
title_short Unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I
title_sort unified approach to prenylated indole alkaloids: total syntheses of (–)-17-hydroxy-citrinalin b, (+)-stephacidin a, and (+)-notoamide i
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4583210/
https://www.ncbi.nlm.nih.gov/pubmed/26417428
http://dx.doi.org/10.1039/c5sc01977j
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