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Published on: November 23, 2016
Total Synthesis of Asperaculin A
Toyoharu Kobayashi1, Yuya Teshigahara1, Momoyo Sakakibara1
1School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, Japan.
Abstract:
The racemic total synthesis of asperaculin A, a sesquiterpenoid lactone with an unprecedented structure, has been accomplished in 17 steps from 3-methyl-2-cyclopentenone. Key features of the synthesis are the construction of a central all-carbon quaternary center using the Johnson-Claisen rearrangement, stereocontrolled introduction of a cyano group, and acid-mediated γ-lactonization.
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