ISSN:
1434-193X
Keywords:
β-Turn mimetic
;
Conformational analysis
;
Synthesis design
;
Tetrahydrofuran
;
THF amino acid
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N- and C-protected derivatives of 2,5-disubstituted trans- and cis-THF amino acids 6 and 7 were prepared in enantiomerically pure form from L-alanine. Felkin-Anh-controlled reduction of the ketone 9 was achieved with a 85:15 diastereoselectivity. Epoxidation of 10 and subsequent intramolecular epoxide opening gave the trans- and cis-THF alcohols 11 and 12, which were further transformed into the corresponding N- and C-protected 2,5-disubstituted trans- and cis-THF amino acids. Conformational studies show that the cis-THF diamide 34 is a β-turn mimetic in the solid state and in CDCl3 solution.Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2046/1999/99165_s.pdf or from the author.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
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