Total syntheses of ent-hypocoprin A and ent-hypocoprin B

This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, construction of the ten-membered ring via the intram...

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Detalles Bibliográficos
Autores principales: Ota, Koichiro, Watanabe, Taiki, Igarashi, Shuntaro, Okazaki, Shinnosuke, Kamaike, Kazuo, Miyaoka, Hiroaki
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/PMC9169068/
https://www.ncbi.nlm.nih.gov/pubmed/35754888
http://dx.doi.org/10.1039/d2ra02891c
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author Ota, Koichiro
Watanabe, Taiki
Igarashi, Shuntaro
Okazaki, Shinnosuke
Kamaike, Kazuo
Miyaoka, Hiroaki
author_facet Ota, Koichiro
Watanabe, Taiki
Igarashi, Shuntaro
Okazaki, Shinnosuke
Kamaike, Kazuo
Miyaoka, Hiroaki
author_sort Ota, Koichiro
collection PubMed
description This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, construction of the ten-membered ring via the intramolecular S(N)2 reaction promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene, and osmium-mediated π-facial selective dihydroxylation to functionalize the 1,1-disubstituted alkene.
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spelling pubmed-91690682022-06-23 Total syntheses of ent-hypocoprin A and ent-hypocoprin B Ota, Koichiro Watanabe, Taiki Igarashi, Shuntaro Okazaki, Shinnosuke Kamaike, Kazuo Miyaoka, Hiroaki RSC Adv Chemistry This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, construction of the ten-membered ring via the intramolecular S(N)2 reaction promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene, and osmium-mediated π-facial selective dihydroxylation to functionalize the 1,1-disubstituted alkene. The Royal Society of Chemistry 2022-06-06 /pmc/articles/PMC9169068/ /pubmed/35754888 http://dx.doi.org/10.1039/d2ra02891c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Ota, Koichiro
Watanabe, Taiki
Igarashi, Shuntaro
Okazaki, Shinnosuke
Kamaike, Kazuo
Miyaoka, Hiroaki
Total syntheses of ent-hypocoprin A and ent-hypocoprin B
title Total syntheses of ent-hypocoprin A and ent-hypocoprin B
title_full Total syntheses of ent-hypocoprin A and ent-hypocoprin B
title_fullStr Total syntheses of ent-hypocoprin A and ent-hypocoprin B
title_full_unstemmed Total syntheses of ent-hypocoprin A and ent-hypocoprin B
title_short Total syntheses of ent-hypocoprin A and ent-hypocoprin B
title_sort total syntheses of ent-hypocoprin a and ent-hypocoprin b
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9169068/
https://www.ncbi.nlm.nih.gov/pubmed/35754888
http://dx.doi.org/10.1039/d2ra02891c
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