A short diastereoselective synthesis of the (±)-rishirilide B core structure |
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Authors: | Junhua Wang |
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Affiliation: | Department of Chemistry and Biochemistry, University of California, Rm 2146, Santa Barbara, CA 93106-9510, USA |
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Abstract: | A series of diastereoselective reactions are reported to form the core of (±)-rishirilide B. The key reactions include: (1) a regioselective tautomerization and etherification of an asymmetric cyclohexa-1,3-dione, (2) an alkoxide directed 1,2-addition of an organometallic reagent and carbamate cleavage and protonation sets two stereocenters, and (3) a novel RuO4 cleavage of an α-hydroxy vinyl ether provides the α-hydroxy ester. |
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Keywords: | Natural product synthesis Enol ether cleavage |
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