Organic Letters
Organic Letters
5 years ago

Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine

Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine
Haichao Liu, Yongfan Ma, Mallesham Pitchakuntla, Xiwu Zhang, Dong Shan, Yanxing Jia
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01504

DOI: 10.1021/acs.orglett.7b01504

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