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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Total Synthesis of Allolaurinterol
Takumi Kurashima1, Kazuki Usuguchi1, Shohei Hamada1
1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-Machi, Kanazawa920-1192, Japan.
Abstract:
The total synthesis of allolaurinterol was accomplished. The cyclopentanone ring was formed via Sc(OTf)3-catalyzed intramolecular cyclization of β-keto esters as the key reaction, which was developed based on the 1,3-rearrangement of cyclic enol ethers. While methylation at the C(2') position afforded a stereoisomeric mixture, the undesired epimer at C(2') was recycled through epimerization via thermodynamic enolate formation followed by a kinetic protonation, thereby improving synthetic efficiency. Consequently, allolaurinterol was obtained from m-cresol in 11 steps with an overall yield of 7%.
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