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Updated: Jun 15, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Bioinspired Total Synthesis of 3-epi-Junipercedrol
Jian Xiao1, Zi-Hao Liu2, Zi-Fan He1
1School of Chemistry, Key Laboratory of Advanced Technologies of Material, Ministry of Education, Southwest Jiaotong University, Chengdu 610031, P. R. China.
Abstract:
A bioinspired total synthesis of 3-epi-junipercedrol, which contains a strained tricyclo[5.2.2.03,7]undecane allo-cedrane framework and five stereocenters, was accomplished via an effective anionic semipinacol rearrangement of a tricyclic cedrane mesylate. The corresponding cedrane precursor was synthesized efficiently by employing the reductive oxy-Nazarov cyclization and an intramolecular aldol condensation as the key steps. This synthetic approach provided a further evidence for the biogenetic relationship between the typical cedrane and allo-cedrane sesquiterpenoids.
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