Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes via gold(i)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates. The resultant compounds could then undergo interrupted Nazarov cy...

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Autores principales: Liao, Hongze, Leng, Wei-Lin, Le Mai Hoang, Kim, Yao, Hui, He, Jingxi, Voo, Amanda Ying Hui, Liu, Xue-Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5625258/
https://www.ncbi.nlm.nih.gov/pubmed/28989693
http://dx.doi.org/10.1039/c7sc02625k
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author Liao, Hongze
Leng, Wei-Lin
Le Mai Hoang, Kim
Yao, Hui
He, Jingxi
Voo, Amanda Ying Hui
Liu, Xue-Wei
author_facet Liao, Hongze
Leng, Wei-Lin
Le Mai Hoang, Kim
Yao, Hui
He, Jingxi
Voo, Amanda Ying Hui
Liu, Xue-Wei
author_sort Liao, Hongze
collection PubMed
description Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes via gold(i)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates. The resultant compounds could then undergo interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[5.3.1.0]undecanes.
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spelling pubmed-56252582017-10-06 Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals Liao, Hongze Leng, Wei-Lin Le Mai Hoang, Kim Yao, Hui He, Jingxi Voo, Amanda Ying Hui Liu, Xue-Wei Chem Sci Chemistry Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes via gold(i)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates. The resultant compounds could then undergo interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[5.3.1.0]undecanes. Royal Society of Chemistry 2017-09-01 2017-08-07 /pmc/articles/PMC5625258/ /pubmed/28989693 http://dx.doi.org/10.1039/c7sc02625k Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Liao, Hongze
Leng, Wei-Lin
Le Mai Hoang, Kim
Yao, Hui
He, Jingxi
Voo, Amanda Ying Hui
Liu, Xue-Wei
Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
title Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
title_full Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
title_fullStr Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
title_full_unstemmed Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
title_short Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
title_sort asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5625258/
https://www.ncbi.nlm.nih.gov/pubmed/28989693
http://dx.doi.org/10.1039/c7sc02625k
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