Total Syntheses of Festuclavine, Pyroclavine, Costaclavine,epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and DihydrosetoclavineClick to copy article linkArticle link copied!
- Haichao Liu†
- ,
- Xiwu Zhang†
- ,
- Dong Shan†
- ,
- Mallesham Pitchakuntla†
- ,
- Yongfan Ma†
- , and
- Yanxing Jia*†‡
Organic Letters
Abstract
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.
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Supporting Information
The Supporting Information is available free of charge on theACS Publications website at DOI:10.1021/acs.orglett.7b01504.
Full experimental procedures and1H and13C NMR spectra of compounds1–8,13–15, and19–27 (PDF)
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Organic Letters
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