Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes

An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the...

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Autores principales: Wang, Li, Shou, Ping-Ping, Wei, Si-Ping, Zhang, Chun, Li, Shuang-Xun, Liu, Ping-Xian, Du, Xi, Wang, Qin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274458/
https://www.ncbi.nlm.nih.gov/pubmed/26797597
http://dx.doi.org/10.3390/molecules21010112
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author Wang, Li
Shou, Ping-Ping
Wei, Si-Ping
Zhang, Chun
Li, Shuang-Xun
Liu, Ping-Xian
Du, Xi
Wang, Qin
author_facet Wang, Li
Shou, Ping-Ping
Wei, Si-Ping
Zhang, Chun
Li, Shuang-Xun
Liu, Ping-Xian
Du, Xi
Wang, Qin
author_sort Wang, Li
collection PubMed
description An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps.
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spelling pubmed-62744582018-12-28 Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes Wang, Li Shou, Ping-Ping Wei, Si-Ping Zhang, Chun Li, Shuang-Xun Liu, Ping-Xian Du, Xi Wang, Qin Molecules Article An enantioselective total synthesis of chiral falcarindiol analogues from buta-1,3-diyn-1-yltriisopropylsilane is reported. The key step in this synthesis is BINOL-promoted asymmetric diacetylene addition to aldehydes. The two chiral centers of the falcarindiol analogues can be produced by using the same kind of catalyst with high selectivity, and the final product can be obtained in only six steps. MDPI 2016-01-19 /pmc/articles/PMC6274458/ /pubmed/26797597 http://dx.doi.org/10.3390/molecules21010112 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Li
Shou, Ping-Ping
Wei, Si-Ping
Zhang, Chun
Li, Shuang-Xun
Liu, Ping-Xian
Du, Xi
Wang, Qin
Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes
title Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes
title_full Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes
title_fullStr Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes
title_full_unstemmed Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes
title_short Total Synthesis of Chiral Falcarindiol Analogues Using BINOL-Promoted Alkyne Addition to Aldehydes
title_sort total synthesis of chiral falcarindiol analogues using binol-promoted alkyne addition to aldehydes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274458/
https://www.ncbi.nlm.nih.gov/pubmed/26797597
http://dx.doi.org/10.3390/molecules21010112
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