Synthetic studies on antibiotic validamycins. Part 11. Synthesis of validamycin A

Synthetic studies on antibiotic validamycins. Part 11. Synthesis of validamycin A
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抗生素井冈霉素的合成研究。

DOI:
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发表时间:
1985
期刊:
影响因子:
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通讯作者:
T. Suami
T. Suami
中科院分区:
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文献类型:
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作者:
S. Ogawa;T. Nose;T. Ogawa;T. Toyokuni;Y. Iwasawa;T. Suami

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抗生素井冈霉素A(1a)是首次合成的(以其十一碳-O-乙酸酯形式),其方法是用2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氯(11)将部分保护的糖苷配基衍生物(8),井冈羟胺A(2a)进行糖基化,然后脱保护,从而建立了先前指定的结构。7-脱氧井冈霉素A的完全O-乙酰化的衍生物(19)也以类似的方式合成。
The antibiotic validamycin A (1a) has been synthesized for the first time (as its undeca-O-acetate) by glycosylation of the partially protected derivative (8) of the aglycone, validoxylamine A (2a), with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride (11), followed by deprotection, thereby establishing the structure previously assigned. The totally O-acetytated derivative (19) of 7-deoxyvalidemycin A has been synthesized in a similar fashion.