Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B

The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6–7 steps using an easily accessible meso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B–C ring and the all-carbon quaternary stereocenter at C-6 were prepared via a desymmetric intramolecula...

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Autores principales: Lu, Xiao-Long, Qiu, Yuanyou, Yang, Baochao, He, Haibing, Gao, Shuanhu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179641/
https://www.ncbi.nlm.nih.gov/pubmed/34168753
http://dx.doi.org/10.1039/d0sc07089k
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author Lu, Xiao-Long
Qiu, Yuanyou
Yang, Baochao
He, Haibing
Gao, Shuanhu
author_facet Lu, Xiao-Long
Qiu, Yuanyou
Yang, Baochao
He, Haibing
Gao, Shuanhu
author_sort Lu, Xiao-Long
collection PubMed
description The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6–7 steps using an easily accessible meso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B–C ring and the all-carbon quaternary stereocenter at C-6 were prepared via a desymmetric intramolecular Michael reaction with up to 97% ee. The naphthalene diol D–E ring was constructed through a sequence of Ti(Oi-Pr)(4)-promoted photoenolization/Diels–Alder, dehydration, and aromatization reactions. This asymmetric strategy provides a scalable route to prepare target molecules and their derivatives for further biological studies.
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spelling pubmed-81796412021-06-23 Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B Lu, Xiao-Long Qiu, Yuanyou Yang, Baochao He, Haibing Gao, Shuanhu Chem Sci Chemistry The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6–7 steps using an easily accessible meso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B–C ring and the all-carbon quaternary stereocenter at C-6 were prepared via a desymmetric intramolecular Michael reaction with up to 97% ee. The naphthalene diol D–E ring was constructed through a sequence of Ti(Oi-Pr)(4)-promoted photoenolization/Diels–Alder, dehydration, and aromatization reactions. This asymmetric strategy provides a scalable route to prepare target molecules and their derivatives for further biological studies. The Royal Society of Chemistry 2021-02-19 /pmc/articles/PMC8179641/ /pubmed/34168753 http://dx.doi.org/10.1039/d0sc07089k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Lu, Xiao-Long
Qiu, Yuanyou
Yang, Baochao
He, Haibing
Gao, Shuanhu
Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
title Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
title_full Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
title_fullStr Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
title_full_unstemmed Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
title_short Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
title_sort asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones a and b
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179641/
https://www.ncbi.nlm.nih.gov/pubmed/34168753
http://dx.doi.org/10.1039/d0sc07089k
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AT yangbaochao asymmetrictotalsynthesisofxestoquinoneandadociaquinonesaandb
AT hehaibing asymmetrictotalsynthesisofxestoquinoneandadociaquinonesaandb
AT gaoshuanhu asymmetrictotalsynthesisofxestoquinoneandadociaquinonesaandb

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