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Total synthesis of the tetracyclic indole alkaloid ht-13-B
Yilin Zhang1, Jeremiah W Hubbard1, Novruz G Akhmedov1
1C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, United States.
The Journal of Organic Chemistry
|March 28, 2015
Abstract:
An expedient synthesis corroborating the proposed structure of the tetracyclic indole alkaloid ht-13-B is presented. Key synthetic steps include acyliminium ion allylation, a Mitsunobu reaction, a palladium-catalyzed Stille-Kelly cross coupling reaction, and a carbon monoxide-mediated palladium-catalyzed reductive N-heterocyclization. The chiral centers are ultimately derived from commercially available trans-4-hydroxy-l-proline.