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Total Synthesis of Highly Oxygenated Bisabolane Sesquiterpene Isolated from Ligularia lankongensis: Relative and Absolute Configurations of the Natural Product
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-01-08 00:00:00 , DOI: 10.1021/acs.joc.7b02688
Kenichi Kobayashi 1 , Risako Kunimura 1 , Hirokazu Takagi 2 , Misaki Hirai 2 , Hiroshi Kogen 1 , Hiroshi Hirota 3 , Chiaki Kuroda 2
Affiliation  

The relative and absolute configurations of an oxygenated bisabolane natural product, isolated from Ligularia lankongensis, were determined by synthesis. All four possible stereoisomers and their tiglate analogues were synthesized from R-(−)-carvone, and their 1H and 13C NMR spectra were compared to establish the 6R,8S,10S configuration. The stereoselective synthesis of the natural product was also achieved, featuring Brown allylation, vanadium-catalyzed epoxidation, and the Mitsunobu reaction.

中文翻译:

高度氧化Bisabolane倍半萜从隔离的全合成橐lankongensis天然产物的相对和绝对构型:

含氧bisabolane天然产品的相对和绝对构型中,从分离橐lankongensis,被合成来确定。从R -(-)-香芹酮合成了所有四种可能的立体异构体及其tiglate类似物,并比较了它们的1 H和13 C NMR光谱以建立6 R,8 S,10 S构型。还实现了天然产物的立体选择性合成,其特征在于布朗烯丙基化,钒催化的环氧化和Mitsunobu反应。
更新日期:2018-01-08
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