Synthesis of (+/-)-secosyrin 1 and a formal synthesis of (-)-secosyrin 1 |
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Authors: | Donohoe Timothy J Fisher John W Edwards Paul J |
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Affiliation: | Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. timothy.donohoe@chem.ox.ac.uk |
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Abstract: | [reaction: see text] A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary. |
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