- Synthesis of sphingosine relatives, XXI. - Synthesis of sphingofungin D and its three diastereomers
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Sphingofungin D [(2S,3R,4R,5S,14R)-1] and its three diastereomers were synthesized by starting from (R)-1,2 epoxyoctane [(R)-7], 1-heptyne (8) and N-acetyl-D-mannosamine (9).
- Otaka, Ken,Mori, Kenji
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p. 1795 - 1802
(2007/10/03)
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- Synthesis of sphingofungin D and its stereoisomer at C-14
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Sphingofungin D (1), a new antifungal agent, and its stereoisomer at C-14 were synthesized by starting from 1-heptyne (5), (R)-1,2-epoxyoctane (6) and N-acetyl D-mannosamine (7).
- Mori, Kenji,Otaka, Ken
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p. 9207 - 9210
(2007/10/02)
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- Malonofungin: an antifungal aminomalonic acid from Phaeoramularia fusimaculans.
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In screening for antifungal metabolites, a novel compound, malonofungin, exhibiting growth inhibitory activity against Botrytis cinerea (grey mould), has been isolated from fermentations of Phaeoramularia fusimaculans CBS 616.87. Its structure is established as (E)-(3R,4S,5S)-5-acetoxy-2-amino-2-carboxy-3,4-dihydroxy-14-oxoicos++ +-6-enoic acid, representing an addition to the rare class of naturally occurring aminomalonic acids. 1H NMR data and extensive use of CD spectroscopy have been utilized to establish the absolute stereochemistry of malonofungin. The structural and biological relationship of malonofungin to previously reported fungal metabolites is discussed.
- Berova,Breinholt,Jensen,Kjaer,Lo,Nakanishi,Nielsen,Olsen,Pedersen,Stidsen
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p. 240 - 251
(2007/10/02)
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- 2-Acetamido-2-deoxyaldonolactones from sugar formazans
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A new approach towards simple aldonic acid derivatives starting from the corresponding aldoses via the 2-acetamido-2-deoxy formazans resulted in the synthesis of 2-acetamido-2-deoxy-D-galactono-1,4-lactone (8), and its 6-deoxy (11) and 6-azido-6-deoxy (14) analogues on treatment with trifluoroacetic acid.The five-membered ring structure of the lactones and that of the intermediate lactone phenylhydrazone (7) was proved by 1H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.With sodium borohydride, lactones 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) and its 6-deoxy analogue (17), respectively.
- Zsoldos-Mady, Virag,Pinter, Istvan,Neszmelyi, Andras,Messmer, Andras,Perczel, Andras
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