Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction

An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement...

Descripción completa

Detalles Bibliográficos
Autores principales: Huang, Yuan, Xue, Fanglin, Liu, Hengmao, Xue, Fei, Liu, Xiao-Yu, Song, Hao, Qin, Yong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Singapore 2020
Materias:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7933312/
https://www.ncbi.nlm.nih.gov/pubmed/33155164
http://dx.doi.org/10.1007/s13659-020-00276-8
_version_ 1783660582937821184
author Huang, Yuan
Xue, Fanglin
Liu, Hengmao
Xue, Fei
Liu, Xiao-Yu
Song, Hao
Qin, Yong
author_facet Huang, Yuan
Xue, Fanglin
Liu, Hengmao
Xue, Fei
Liu, Xiao-Yu
Song, Hao
Qin, Yong
author_sort Huang, Yuan
collection PubMed
description An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter. [Image: see text]
format Online
Article
Text
id pubmed-7933312
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Springer Singapore
record_format MEDLINE/PubMed
spelling pubmed-79333122021-03-19 Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction Huang, Yuan Xue, Fanglin Liu, Hengmao Xue, Fei Liu, Xiao-Yu Song, Hao Qin, Yong Nat Prod Bioprospect Short Communication An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter. [Image: see text] Springer Singapore 2020-11-05 /pmc/articles/PMC7933312/ /pubmed/33155164 http://dx.doi.org/10.1007/s13659-020-00276-8 Text en © The Author(s) 2020 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Short Communication
Huang, Yuan
Xue, Fanglin
Liu, Hengmao
Xue, Fei
Liu, Xiao-Yu
Song, Hao
Qin, Yong
Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction
title Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction
title_full Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction
title_fullStr Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction
title_full_unstemmed Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction
title_short Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction
title_sort asymmetric total synthesis of (+)-21-epi-eburnamonine via a photocatalytic radical cascade reaction
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7933312/
https://www.ncbi.nlm.nih.gov/pubmed/33155164
http://dx.doi.org/10.1007/s13659-020-00276-8
work_keys_str_mv AT huangyuan asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction
AT xuefanglin asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction
AT liuhengmao asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction
AT xuefei asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction
AT liuxiaoyu asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction
AT songhao asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction
AT qinyong asymmetrictotalsynthesisof21epieburnamonineviaaphotocatalyticradicalcascadereaction

Ejemplares similares