Organic Letters · 2014 · 75 citations · 43 references
Communesin FMedicinal ChemistryEngineeringBiochemistryNatural SciencesDiastereodivergent Synthetic StrategyComplementary Relative StereochemistryOrganic ChemistryStereodivergent ApproachStereoselective SynthesisChemistryNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations.
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Communesins, cytotoxic metabolites of a fungus isolated from a marine alga
Atsushi Numata, Chika Takahashi, Yoshinori Ito et al. · Tetrahedron Letters · 1993 · 267 citations
Total Synthesis of (±)-Communesin F
Jun Yang, Haoxing Wu, Liqun Shen et al. · Journal of the American Chemical Society · 2007 · 211 citations
Sandy Ma, Xiaoqing Han, Shyam Krishnan et al. · Angewandte Chemie International Edition · 2009 · 209 citations
Chemical Engineering, Racemic Tertiary Halooxindoles, Bioorganic Chemistry +13