Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes

[Image: see text] We report the first chemical syntheses of both (−)-majucin and (−)-jiadifenoxolane A via 10 net oxidations from the ubiquitous terpene (+)-cedrol. Additionally, this approach allows for access to other majucin-type sesquiterpenes, like (−)-jiadifenolide, (−)-jiadifenin, and (−)-(1R...

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Autores principales: Condakes, Matthew L., Hung, Kevin, Harwood, Stephen J., Maimone, Thomas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5729088/
https://www.ncbi.nlm.nih.gov/pubmed/29148748
http://dx.doi.org/10.1021/jacs.7b11493
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author Condakes, Matthew L.
Hung, Kevin
Harwood, Stephen J.
Maimone, Thomas J.
author_facet Condakes, Matthew L.
Hung, Kevin
Harwood, Stephen J.
Maimone, Thomas J.
author_sort Condakes, Matthew L.
collection PubMed
description [Image: see text] We report the first chemical syntheses of both (−)-majucin and (−)-jiadifenoxolane A via 10 net oxidations from the ubiquitous terpene (+)-cedrol. Additionally, this approach allows for access to other majucin-type sesquiterpenes, like (−)-jiadifenolide, (−)-jiadifenin, and (−)-(1R,10S)-2-oxo-3,4-dehydroxyneomajucin (ODNM) along the synthetic pathway. Site-selective aliphatic C(sp(3))-H bond oxidation reactions serve as the cornerstone of this work which offers access to highly oxidized natural products from an abundant and renewable terpene feedstock.
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spelling pubmed-57290882017-12-17 Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes Condakes, Matthew L. Hung, Kevin Harwood, Stephen J. Maimone, Thomas J. J Am Chem Soc [Image: see text] We report the first chemical syntheses of both (−)-majucin and (−)-jiadifenoxolane A via 10 net oxidations from the ubiquitous terpene (+)-cedrol. Additionally, this approach allows for access to other majucin-type sesquiterpenes, like (−)-jiadifenolide, (−)-jiadifenin, and (−)-(1R,10S)-2-oxo-3,4-dehydroxyneomajucin (ODNM) along the synthetic pathway. Site-selective aliphatic C(sp(3))-H bond oxidation reactions serve as the cornerstone of this work which offers access to highly oxidized natural products from an abundant and renewable terpene feedstock. American Chemical Society 2017-11-17 2017-12-13 /pmc/articles/PMC5729088/ /pubmed/29148748 http://dx.doi.org/10.1021/jacs.7b11493 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Condakes, Matthew L.
Hung, Kevin
Harwood, Stephen J.
Maimone, Thomas J.
Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
title Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
title_full Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
title_fullStr Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
title_full_unstemmed Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
title_short Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
title_sort total syntheses of (−)-majucin and (−)-jiadifenoxolane a, complex majucin-type illicium sesquiterpenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5729088/
https://www.ncbi.nlm.nih.gov/pubmed/29148748
http://dx.doi.org/10.1021/jacs.7b11493
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