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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
A concise synthesis of marine natural product (-)-15-oxopuupehenol from (+)-sclarelide
Yun-Fei Cheng1, Hui-Jing Li1,2, Yin-Lin Zhang1
1Weihai Marine Organism & Medical Technology Research Institute, Harbin Institute of Technology, Weihai, P. R. China.
Abstract:
A step-economical synthesis of (-)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford α, β-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (-)-15-oxopuupehenol.
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