Date of Graduation
2004
Document Type
Thesis
Degree Type
MS
Committee Chair
Bjorn C. G. Soderberg
Abstract
A mild and efficient route for the synthesis of substituted carbazolones has been developed. This novel procedure includes two consecutive palladium-catalyzed reactions, an intermolecular Stille coupling followed by an intramolecular reductive Nheteroannulation. This new approach was successfully applied to the formal total synthesis of several naturally occurring carbazole alkaloids including clausenol, clausenine, clausalene and glycozoticine. These new syntheses are generally effective and produce carbazolones in high overall yields. In addition, all attempts to apply a similar method to the synthesis of 1-substituted βcarbolines produced impure products.
Recommended Citation
Yu, Xiaomei, "Formal total synthesis of carbazole alkaloids and attempted synthesis of 1-substituted β-carbolines." (2004). Graduate Theses, Dissertations, and Problem Reports (ETD). 10822.
https://researchrepository.wvu.edu/etd/10822