Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
J Am Chem Soc. 2017 Dec 13;139(49):17783-17786. doi: 10.1021/jacs.7b11493. Epub 2017 Nov 26.
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)-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.
我们首次通过从普遍存在的萜烯 (+)-柏木醇进行 10 次净氧化反应，合成了（-）-马朱辛和（-）-加地芬诺烷 A。此外，这种方法还可以通过该合成途径获得其他马朱辛型倍半萜，如（-）-加地酚内酯、（-）-加地芬宁和（-）-（1R，10S）-2-氧代-3，4-去氢新马朱辛（ODNM）。选择性的脂肪族 C(sp)-H 键氧化反应是这项工作的基石，它可以从丰富的可再生萜烯原料中获得高度氧化的天然产物。
