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Updated: May 1, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Divergent Asymmetric Total Synthesis of the cis-Clerodane Diterpenoids
1Department of Chemistry, University of Konstanz, Konstanz 78464, Germany.
Abstract:
Herein we describe the first asymmetric total synthesis of five cis-clerodane diterpenoids, scaparvins B-D and parvitexins B-C. The strategy features a TEMPO+BF4--mediated lactonization, first discovered in this work, to construct the cis-5/6-fused bicyclic ring system, followed by a stereoselective intramolecular nitrile oxide-alkene [3 + 2] cycloaddition to establish the cis-decalin core. Subsequent Stille coupling and ketalization enabled the assembly of the complete carbon skeleton. During the reductive ring-opening of the isoxazoline moiety, unexpected epimerization at C6 was observed, enabling a divergent synthetic strategy. This streamlined strategy may serve as a general blueprint for the synthesis of other members of the clerodane diterpenoid family.
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