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. Author manuscript; available in PMC: 2014 Sep 8.
Published in final edited form as: Nat Chem. 2014 Jan 19;6(2):122–125. doi: 10.1038/nchem.1841

Figure 3. 1,4-Oxygenation of alkene-containing natural products and derivatives.

Figure 3

Application of the developed protocol for conversion of alkene-containing natural products and derivatives into the corresponding 1,4-diols. a, Conversion of Camphene into 1,4-diol 4r; b, Conversion of 2-Methylenebornane (derived from Bornane) into 1,4-diol 4s. c, Conversion of alkene 1t (derived form Lithoholic acid) into 1,4-diol 4t. *Mixture of stereoisomers endo/exo 8:1, major isomer is drawn (for details, see Supplementary Fig. S12). **Mixture of stereoisomers endo/exo 1:3, major isomer is drawn (for details, see Supplementary Fig. S13). THF, tetrahydrofuran; Pic, 2-picolyl; cod, cyclooctadiene; nbe, norbornene; TBAF, tetrabutylammonium fluoride; NMP, N-methylpyrrolidone; RT, room temperature; Ac, acetyl; DMAP, 4-dimethylaminopyridine; DCM, dichloromethane.