Total Syntheses of Phleghenrines A and C

[Image: see text] Herein, we report the total syntheses of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Notable steps include an inverse electron-demand Diels–Alder reaction between a masked o-benzoquinone and a N-protected enamine to prepare o...

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Autores principales: Cai, Xinpei, Li, Lei, Wang, Ye-Cheng, Zhou, Jianhan, Dai, Mingji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10367062/
https://www.ncbi.nlm.nih.gov/pubmed/37432129
http://dx.doi.org/10.1021/acs.orglett.3c01784
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author Cai, Xinpei
Li, Lei
Wang, Ye-Cheng
Zhou, Jianhan
Dai, Mingji
author_facet Cai, Xinpei
Li, Lei
Wang, Ye-Cheng
Zhou, Jianhan
Dai, Mingji
author_sort Cai, Xinpei
collection PubMed
description [Image: see text] Herein, we report the total syntheses of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Notable steps include an inverse electron-demand Diels–Alder reaction between a masked o-benzoquinone and a N-protected enamine to prepare one key intermediate with a bicyclo[2.2.2]octenone core, a Büchner–Curtius–Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner’s modified 2-pyridone synthesis to install the 2-pyridone moiety.
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spelling pubmed-103670622023-07-26 Total Syntheses of Phleghenrines A and C Cai, Xinpei Li, Lei Wang, Ye-Cheng Zhou, Jianhan Dai, Mingji Org Lett [Image: see text] Herein, we report the total syntheses of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Notable steps include an inverse electron-demand Diels–Alder reaction between a masked o-benzoquinone and a N-protected enamine to prepare one key intermediate with a bicyclo[2.2.2]octenone core, a Büchner–Curtius–Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner’s modified 2-pyridone synthesis to install the 2-pyridone moiety. American Chemical Society 2023-07-11 /pmc/articles/PMC10367062/ /pubmed/37432129 http://dx.doi.org/10.1021/acs.orglett.3c01784 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Cai, Xinpei
Li, Lei
Wang, Ye-Cheng
Zhou, Jianhan
Dai, Mingji
Total Syntheses of Phleghenrines A and C
title Total Syntheses of Phleghenrines A and C
title_full Total Syntheses of Phleghenrines A and C
title_fullStr Total Syntheses of Phleghenrines A and C
title_full_unstemmed Total Syntheses of Phleghenrines A and C
title_short Total Syntheses of Phleghenrines A and C
title_sort total syntheses of phleghenrines a and c
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10367062/
https://www.ncbi.nlm.nih.gov/pubmed/37432129
http://dx.doi.org/10.1021/acs.orglett.3c01784
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AT zhoujianhan totalsynthesesofphleghenrinesaandc
AT daimingji totalsynthesesofphleghenrinesaandc

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