Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage

We report herein a highly efficient strategy for construction of a bridged oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton through [3 + 2] IMCC (intramolecular [3 + 2] cross-cycloaddition), and the substituents and/or stereochemistries on C-4, C-6, C-7 and C-10 fully match those in the rh...

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Detalles Bibliográficos
Autores principales: Cui, Yi, Lv, Jiayuan, Song, Tianhang, Ren, Jun, Wang, Zhongwen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8985103/
https://www.ncbi.nlm.nih.gov/pubmed/35424922
http://dx.doi.org/10.1039/d2ra01315k
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author Cui, Yi
Lv, Jiayuan
Song, Tianhang
Ren, Jun
Wang, Zhongwen
author_facet Cui, Yi
Lv, Jiayuan
Song, Tianhang
Ren, Jun
Wang, Zhongwen
author_sort Cui, Yi
collection PubMed
description We report herein a highly efficient strategy for construction of a bridged oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton through [3 + 2] IMCC (intramolecular [3 + 2] cross-cycloaddition), and the substituents and/or stereochemistries on C-4, C-6, C-7 and C-10 fully match those in the rhamnofolane, tigliane and daphnane diterpenoids. Furthermore, ring-opening of the bridged oxa-[3.2.1]octane via C–O bond cleavage was also successfully achieved.
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spelling pubmed-89851032022-04-13 Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage Cui, Yi Lv, Jiayuan Song, Tianhang Ren, Jun Wang, Zhongwen RSC Adv Chemistry We report herein a highly efficient strategy for construction of a bridged oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton through [3 + 2] IMCC (intramolecular [3 + 2] cross-cycloaddition), and the substituents and/or stereochemistries on C-4, C-6, C-7 and C-10 fully match those in the rhamnofolane, tigliane and daphnane diterpenoids. Furthermore, ring-opening of the bridged oxa-[3.2.1]octane via C–O bond cleavage was also successfully achieved. The Royal Society of Chemistry 2022-03-25 /pmc/articles/PMC8985103/ /pubmed/35424922 http://dx.doi.org/10.1039/d2ra01315k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Cui, Yi
Lv, Jiayuan
Song, Tianhang
Ren, Jun
Wang, Zhongwen
Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage
title Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage
title_full Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage
title_fullStr Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage
title_full_unstemmed Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage
title_short Highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via C–O bond cleavage
title_sort highly efficient construction of an oxa-[3.2.1]octane-embedded 5–7–6 tricyclic carbon skeleton and ring-opening of the bridged ring via c–o bond cleavage
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8985103/
https://www.ncbi.nlm.nih.gov/pubmed/35424922
http://dx.doi.org/10.1039/d2ra01315k
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