Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes
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-de...
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| Veröffentlicht in: | Journal of the American Chemical Society 2017-12, Vol.139 (49), p.17783-17786 |
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| container_end_page | 17786 |
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| container_issue | 49 |
| container_start_page | 17783 |
| container_title | Journal of the American Chemical Society |
| container_volume | 139 |
| creator | Condakes, Matthew L Hung, Kevin Harwood, Stephen J Maimone, Thomas J |
| description | 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(sp3)-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. |
| doi_str_mv | 10.1021/jacs.7b11493 |
| format | Article |
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Am. Chem. Soc</addtitle><date>2017-12-13</date><risdate>2017</risdate><volume>139</volume><issue>49</issue><spage>17783</spage><epage>17786</epage><pages>17783-17786</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>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. 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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Biological Products - chemical synthesis Biological Products - chemistry Communication Illicium - chemistry Molecular Structure Oxidation-Reduction Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Terpenes - chemistry |
| title | Total Syntheses of (−)-Majucin and (−)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes |
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