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Divergent and Stereoselective Synthesis of Ustusal A, (-)-Albrassitriol, and Elegansin D
Yue-Cheng Wu1, Guang-Sen Xu2, Hui-Jing Li1,2
1Weihai Marine Organism & Medical Technology Research Institute, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150006, P. R. China.
Abstract:
The first synthesis of ustusal A as well as expeditious access to (-)-albrassitriol is described as featuring a singlet oxygen [4 + 2] cycloaddition, achieving the desired stereoselectivity for the 1,4-cis-hydroxyl groups. Transformation of (+)-sclareolide to III followed by a key Horner-Wadsworth-Emmons (HWE) reaction and stereospecific allylic oxidation facilitated the first synthesis of elegansin D. The biological evaluation of these natural products together with seven elegansin D analogues was performed, among which several elegansin D analogues exhibited potential anticancer activity against liver cancer HepG2 cells (IC50 = 11.99-25.58 μM) with low cytotoxicity on normal liver HL7702 cells (IC50 > 100 μM).
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