Scheme 1 | The Journal of Antibiotics

Scheme 1

From: Ktedonoketone and 2’-oxosattabacin, benzenoid metabolites from a thermophilic bacterium Thermosporothrix hazakensis in the phylum Chloroflexi

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Synthesis of model compounds (Z)- and (E)-12. Reagents and conditions: (a) i-Pr2NEt, PhCHO, n-Bu2BOTf, CH2Cl2 –78 to 0 °C, 14/other diastereomers = 3.6:1; (b) TESOTf, 2,6-lutidine, CH2Cl2, 0 °C to rt, 36% from 13; (c) LiBH4, Et2O, MeOH, 0 °C to rt, 91%.; (d) TEMPO, KBr, aq. NaOCl, NaHCO3, CH2Cl2 0 °C; (e) isobutylmagnesium chloride, THF, 0 °C to rt, dr = 20:1; (f) AZADOL, KBr, aq. NaOCl, NaHCO3; (g) TBAF/AcOH, THF, 0 °C to rt, 49% from 16; (h) PhSeH, ADDP, n-Bu3P, THF, rt; (i) aq. H2O2, NaHCO3,THF, 0 °C, 54% from 18; (j) MgCl2, Et3N, PhCHO, TMSCl, THF, rt, then TFA, MeOH, rt, 14’/other diastereomers = 1.8:1

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