Antibiotics from Gliding Bacteria, LXXIX. – Chemical Modification of the Antifungal Macrolide Soraphen A1α: Deoxygenation in the South-East Ring Segment
✍ Scribed by Kiffe, Michael ;Schummer, Dietmar ;Höfle, Gerhard
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 937 KB
- Volume
- 1997
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The present paper describes the chemical modification of the antifungal macrolide soraphen A~1α~ (1) by selective removal of oxygen substituents in the south‐east ring segment. In the course of this investigation two key derivatives were prepared: 4‐demethyl‐5‐O‐(4‐methoxybenzyl)‐4‐episoraphen (6) and 3,5‐dideoxy‐4‐oxosoraphen (22). 6 served as precursor for 4‐demethoxysoraphen (19) and 4‐demethoxy‐5‐deoxysoraphen (20). 22 was used for the deoxygenation in positions C‐3, C‐4 and C‐5 and for the synthesis of 3,5‐didesoxysoraphen (24) as well as 4‐demethoxy‐3,5‐dideoxysoraphen (27). The comparison of the antifungicidal activity of these derivatives showed that the OH group in position C‐3 is essential for the biological activity of the soraphens.