A concise diastereoselective approach to (+)-dexoxadrol, (−)-epi-dexoxadrol, (−)-conhydrine and (+)-lentiginosine from (−)-pipecolinic acid |
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Authors: | Chinmay Bhat Santosh G. Tilve |
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Affiliation: | Department of Chemistry, Goa University, Taleigao-Plateau, Goa 403 206, India |
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Abstract: | A new diastereoselective pathway for the total synthesis of (+)-dexoxadrol, first asymmetric synthesis of (−)-epi-dexoxadrol and formal synthesis of conhydrine and (+)-lentiginosine is presented using commercially available (−)-pipecolinic acid. The key reactions utilized are Sharpless asymmetric dihydroxylation and Wittig reaction. The paper further describes the study of effect of protecting groups on dihydroxylation of a terminal olefin in piperidine ring system. |
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Keywords: | Piperidines Sharpless dihydroxylation Wittig reaction Alkaloids |
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