Synthesis of prumycin
β 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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β¦ 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.
π SIMILAR VOLUMES
## Abstract A number of 3βdeoxyβDLβprumycin analogues containing one or more amino acid moieties were synthesized. Key intermediate 2 afforded ester analogues by coupling with HβDβ or LβAlaβOH, while intermediates 6 and 9 afforded amide analogues by coupling with HβDβAlaβDβAlaβOH, HβDβAlaβOH, 2βami
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