ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of threo-cis/threo-trans- and erythro-cis/erythro-trans-dihydropalustrinThe first synthesis of a threefold protected spermidine, namely 3-benzyloxycarbonyl-N1-phthaloyl-N2-tosylspermidin (9) is presented. Each of the protecting groups can be removed selectively. After hydrazinolysis the resulting N3-benzyloxy-carbonyl-N2-tosylspermidine (10) has been condensed with methyl (2 E)-cis-7,8-epoxy-2-decenoate to the threo-cis/trans piperidines 17, and with methyl (2 E)-trans-7,8-epoxy-2-decenoate to the erythro-cis/trans piperidines 17, respectively. After catalytic removal of the Z group, the resulting aminoesters 13 and 18, in a melt with imidazole, underwent ring closure to the 13-membered lactames 14 and 19, respectively. reductive deprotection of the N-tosyl group with sodium/ammonia led to the stereoisomeric palustrines 15 and 20, respectively.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19780610240
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