Completely stereocontrolled synthesis of the right fragment of salinomycin,a polyether antibiotic,by means of the chelation-controlled grignard reaction |
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Authors: | Yuji Oikawa Kiyoshi Horita Osamu Yonemitsu |
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Institution: | Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan |
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Abstract: | In the course of our synthetic study of salinomycin (), an ionophorous polyether antibiotic, the γ-lactone () corresponding to the C-21~C-30 fragment (the right fragment) of was synthesized from D-mannitol and ethyl L-lactate as chiral starting materials. The complete stereocontrol for the construction of new chiral centers has been achieved by means of the chelation-controlled Grignard reaction and the tetrahydropyran synthesis via the acid catalyzed epoxide ring opening. |
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