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Synthesis and Antifungal Activity of 3-Deoxy-DL-prumycin Analogues

โœ Scribed by Constantinou-Kokotou, Violetta ;Kokotos, George ;Chrysayi-Tokousbalides, Maria ;Couladouros, Elias A. ;Georgiadis, Minas P.

Book ID
102366384
Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
373 KB
Volume
1994
Category
Article
ISSN
0947-3440

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โœฆ Synopsis

Abstract

A number of 3โ€deoxyโ€DLโ€prumycin analogues containing one or more amino acid moieties were synthesized. Key intermediate 2 afforded ester analogues by coupling with Hโ€Dโ€ or Lโ€Alaโ€OH, while intermediates 6 and 9 afforded amide analogues by coupling with Hโ€Dโ€Alaโ€Dโ€Alaโ€OH, Hโ€Dโ€Alaโ€OH, 2โ€aminoโ€4,4โ€dichlorobutanoic acid and acetic acid. The antifungal activity of the analogues against various phytopathogenic fungi was measured. magnified image

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โœ Violetta Constantinou-Kokotou; Elias A. Couladouros; Minas P. Georgiadis; George ๐Ÿ“‚ Article ๐Ÿ“… 1991 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 726 KB

3-Deoxy-DL-prumycin (1) was synthesized from 2-furanmethanol (2-furfuryl alcohol, 2) in eleven steps in 15% total yield. Michael addition of azide anion to 2,3-dideoxy-oqent-2-enopyranos~ulose (3) and reduction in situ of the adduct afforded the key intermediates 5 and 6. Introduction of a second ax