期刊
TETRAHEDRON
卷 61, 期 27, 页码 6527-6533出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.05.004
关键词
stereoselective synthesis; DMDP; polyhydroxylated pyrrolizidines; (+)-casuarine; 6,7-diepicasuarine
A new synthesis for (+)-casuarine (1) and its 6,7-diepi isomer (15) in a stereocontrolled manner, is reported herein. All appropriately protected polyhydroxylated pyrrolidine, such as (2R,3R,4R,5R)-3,4-dibenzyloxy-2'-O-tet-t-butyldiphenylsilyl-2,5-bis(hydroxymethl)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. (c) 2005 Elsevier Ltd. All rights reserved.
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