1. Concise Seven-Membered Oxepene/Oxepane Synthesis – Structural Motifs in Natural and Synthetic Products
- Author
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Jon D. Rainier and Clement Osei Akoto
- Subjects
Olefin metathesis ,010405 organic chemistry ,Organic Chemistry ,010402 general chemistry ,Metathesis ,01 natural sciences ,Adriatoxin ,Combinatorial chemistry ,Catalysis ,Wilkinson's catalyst ,0104 chemical sciences ,Oxepane ,chemistry.chemical_compound ,chemistry ,Structural motif - Abstract
This work outlines a suitable method for the synthesis of oxepane skeleton using iterative C-glycoside technology on the oxepene intermediate, which was synthesized utilizing Wilkinson’s catalyst [Rh(PPh3)3Cl] to generate the isomerized product in a linear synthetic manner. The central core of the oxepene motif was achieved via an olefin metathesis reaction using the Grubbs second-generation and Schrock catalysts. The synthesis of the functionalized oxepane having the desired adriatoxin E-ring relative stereochemistry was achieved starting from commercially available homopropargylic alcohol. more...
- Published
- 2019
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