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Synthesis of prumycin

✍ Scribed by Hiroyoshi Kuzuhara; Sakae Emoto


Book ID
104215179
Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
230 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis


Prumycin is a new antifungal antibiotic isolated as a dihydrochloride by Hata et al. 1) in 1971. It strongly inhibits the growth of phytopathogenic fungi such as Scterotinia sclerothrwn and Botorytis fabae. The structure of prumycin was recently elucidated to be 4-D- alanylamino-2-amino-2.4-dideoxy-L-arabinopyranose by Ohsura et al.. 21 We wish to describe here the synthesis of prumycin dihydrochloride ( I 1. This is the first synthesis of the antibiotic.


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## Abstract A number of 3‐deoxy‐DL‐prumycin analogues containing one or more amino acid moieties were synthesized. Key intermediate 2 afforded ester analogues by coupling with H‐D‐ or L‐Ala‐OH, while intermediates 6 and 9 afforded amide analogues by coupling with H‐D‐Ala‐D‐Ala‐OH, H‐D‐Ala‐OH, 2‐ami

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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