An efficient synthesis of the 1,6-dioxaspiro[4.4]nonan-2-one motif of the immunosuppressive triterpenoid Phainanoid F |
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| Authors: | Chen-Lu Zhang Fa-Jun Nan |
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| Affiliation: | National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China;University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, PR China |
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| Abstract: | ![]()
We describe an efficient synthesis of the 1,6-dioxaspiro[4.4]nonan-2-one motif of the immunosuppressive triterpenoid Phainanoid F and its C4 epimer. A furan oxidative spirocyclization for constructing the spiro center was used as the key step. Other important reactions involved Sharpless asymmetric dihydroxylation, Weinreb ketone synthesis and Yamaguchi esterfication. The synthesis was achieved in 11 linear steps with 17.3% overall yield. |
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| Keywords: | Immunosuppressive triterpenoid Phainanoid F Furan Oxidative spirocyclization |
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