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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Total Syntheses of the Cyclobutane-Containing Guaiane-Type Sesquiterpene Daphnepapytone A and Certain Congeners
Shu Xiao1,2, Ping Lan1,2, Srinivas Beduru3
1State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, 510632, China.
Abstract:
Daphnepapytone A (1), a structurally unique guaiane-type sesquiterpenoid, has been prepared by total synthesis. So, a (S)-carvone-derived decalindienone was subjected to a photosantonin rearrangement to afford, after additional steps, the natural product oleodaphnone (9). An intramolecular [2 + 2]-cycloaddition of compound 9 followed by an allylic oxidation then gave target 1. Four other structures assigned to guaianes were prepared by related means and so identifying two errors in the recent literature.
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