Date of Graduation
2016
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Björn C. G. Söderberg
Committee Member
Kung K. Wang
Committee Member
John H. Penn
Committee Member
Glen P. Jackson
Committee Member
Yon Rojanasakul
Abstract
Total synthesis of tetracyclic indole alkaloid ht-13-A and ht-13-B has been accomplished from commercially available (S)-4-amino-2-hydroxybutyric acid and trans4-hydroxy-L-proline respectively. The key synthetic steps include an acyliminium ion allylation, a Mitsunobu reaction, a palladium-catalyzed Stille-Kelly cross coupling reaction, and a carbon monoxide mediated palladium-catalyzed reductive Nheterocyclization. The total synthesis of aurantioclavine has been studied. The synthesis commenced with 2-amino-3-nitrophenol. Key synthetic steps include a Stille coupling reaction, a Heck reaction, a Lewis acid mediated cyclization and a carbon monoxide mediated palladium-catalyzed reductive N-heterocyclization. In addition, the first asymmetric total synthesis of (+)-cycloclavine has been studied. Key synthetic steps include a ring closing metathesis, an acyliminium ion allylation and a Stille coupling.
Recommended Citation
Zhang, Yilin, "Total synthesis of ht-13-A and ht-13-B, total synthesis of aurantioclavine, progress towards the synthesis of cycloclavine" (2016). Graduate Theses, Dissertations, and Problem Reports. 7040.
https://researchrepository.wvu.edu/etd/7040