Festuclavine、Pyroclavine、Costaclavine、epi-Costaclavine、Pibocin A、9-Deacetoxyfumigaclavine C、Fumigaclavine G 和 Dihydrosetoclavine 的全合成。
Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine.
机构信息
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , 38 Xueyuan Road, Beijing 100191, China.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
出版信息
Org Lett. 2017 Jun 16;19(12):3323-3326. doi: 10.1021/acs.orglett.7b01504. Epub 2017 Jun 8.
A new approach for the divergent total synthesis of eight ergot alkaloids is reported. The approach allows the first total syntheses of pyroclavine, pibocin A, 9-deacetoxyfumigaclavine C, and fumigaclavine G and also enables the efficient synthesis of festuclavine, costaclavine, epi-costaclavine, and dihydrosetoclavine. The main feature of the synthesis is the use of an unprecedented Pd-catalyzed intramolecular Larock indole annulation/Tsuji-Trost allylation cascade to assemble the tetracyclic core in one step.
报道了一种新型的麦角生物碱发散全合成方法。该方法实现了吡咯卡林、皮博霉素 A、9-去乙酰氧基麦角菌 C 和麦角菌 G 的首次全合成，同时也高效合成了 festuclavine、costaclavine、epi-costaclavine 和 dihydrosetoclavine。该合成的主要特点是使用了一种前所未有的 Pd 催化的 Larock 吲哚环化/Tsuji-Trost 烯丙基化级联反应，一步构建四环核心。
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