Polyhydroxylated pyrrolizidines. Part 6: A new and concise stereoselective synthesis of (+)-casuarine and its 6,7-diepi isomer, from DMDP |
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Authors: | Isidoro Izquierdo María T Plaza Juan A Tamayo |
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Institution: | Department of Medicinal and Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain |
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Abstract: | A new synthesis for (+)-casuarine (1) and its 6,7-diepi isomer (15) in a stereocontrolled manner, is reported herein. An appropriately protected polyhydroxylated pyrrolidine, such as (2R,3R,4R,5R)-3,4-dibenzyloxy-2′-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (3, protected DMDP), easily available from d-fructose, was chosen as the chiral starting material. Compounds 1 and 15 were obtained from 3, in seven steps, in a 23.2 and 20.5% overall yields, respectively. |
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Keywords: | Stereoselective synthesis DMDP Polyhydroxylated pyrrolizidines (+)-Casuarine 6 7-Diepicasuarine |
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