Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings

Here we describe the diastereoselective synthesis of (5r,8r)‐1,9‐diazadispiro[4.2.4(8).2(5)]tetradecatrienes via domino double spirocyclization of N‐arylamide derivatives. This reaction can serve as a fast way to synthesize diazadispirocycles, which are found in the core structures of bioactive natu...

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Autores principales: Yokoe, Hiromasa, Mizumura, Yuka, Sugiyama, Kana, Yan, Kejia, Hashizume, Yuna, Endo, Yuto, Yoshida, Sae, Kiriyama, Akiko, Tsubuki, Masayoshi, Kanoh, Naoki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756633/
https://www.ncbi.nlm.nih.gov/pubmed/33029940
http://dx.doi.org/10.1002/asia.202001179
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author Yokoe, Hiromasa
Mizumura, Yuka
Sugiyama, Kana
Yan, Kejia
Hashizume, Yuna
Endo, Yuto
Yoshida, Sae
Kiriyama, Akiko
Tsubuki, Masayoshi
Kanoh, Naoki
author_facet Yokoe, Hiromasa
Mizumura, Yuka
Sugiyama, Kana
Yan, Kejia
Hashizume, Yuna
Endo, Yuto
Yoshida, Sae
Kiriyama, Akiko
Tsubuki, Masayoshi
Kanoh, Naoki
author_sort Yokoe, Hiromasa
collection PubMed
description Here we describe the diastereoselective synthesis of (5r,8r)‐1,9‐diazadispiro[4.2.4(8).2(5)]tetradecatrienes via domino double spirocyclization of N‐arylamide derivatives. This reaction can serve as a fast way to synthesize diazadispirocycles, which are found in the core structures of bioactive natural products. Product diversification via Suzuki–Miyaura cross coupling and application to the synthesis of 1‐oxa‐9‐azadispiro[4.2.4(8).2(5)]tetradecatrienes were also conducted.
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spelling pubmed-77566332020-12-28 Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings Yokoe, Hiromasa Mizumura, Yuka Sugiyama, Kana Yan, Kejia Hashizume, Yuna Endo, Yuto Yoshida, Sae Kiriyama, Akiko Tsubuki, Masayoshi Kanoh, Naoki Chem Asian J Communications Here we describe the diastereoselective synthesis of (5r,8r)‐1,9‐diazadispiro[4.2.4(8).2(5)]tetradecatrienes via domino double spirocyclization of N‐arylamide derivatives. This reaction can serve as a fast way to synthesize diazadispirocycles, which are found in the core structures of bioactive natural products. Product diversification via Suzuki–Miyaura cross coupling and application to the synthesis of 1‐oxa‐9‐azadispiro[4.2.4(8).2(5)]tetradecatrienes were also conducted. John Wiley and Sons Inc. 2020-10-23 2020-12-14 /pmc/articles/PMC7756633/ /pubmed/33029940 http://dx.doi.org/10.1002/asia.202001179 Text en © 2020 The Authors. Chemistry - An Asian Journal published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Yokoe, Hiromasa
Mizumura, Yuka
Sugiyama, Kana
Yan, Kejia
Hashizume, Yuna
Endo, Yuto
Yoshida, Sae
Kiriyama, Akiko
Tsubuki, Masayoshi
Kanoh, Naoki
Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
title Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
title_full Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
title_fullStr Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
title_full_unstemmed Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
title_short Rapid Access to Dispirocyclic Scaffolds Enabled by Diastereoselective Intramolecular Double Functionalization of Benzene Rings
title_sort rapid access to dispirocyclic scaffolds enabled by diastereoselective intramolecular double functionalization of benzene rings
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756633/
https://www.ncbi.nlm.nih.gov/pubmed/33029940
http://dx.doi.org/10.1002/asia.202001179
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