TOTAL SYNTHESIS OF PALYTOXIN CARBOXYLIC-ACID AND PALYTOXIN AMIDE
TOTAL SYNTHESIS OF PALYTOXIN CARBOXYLIC-ACID AND PALYTOXIN AMIDE
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DOI：
10.1021/ja00201a038
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发表时间：
1989-09-13
影响因子：
15
通讯作者：
YONAGA, M
中科院分区：
文献类型：
--
作者：
ARMSTRONG, RW;BEAU, JM;YONAGA, M
以完全保护的羽衣藻毒素羧酸为原料，实现了羽衣藻毒素羧酸和羽衣藻酰胺的全合成。完全保护的孢子毒素羧酸1含有8个不同的保护基，共42个保护基。所有这些保护基团都在五个合成操作中被成功地去除，即(1)DDQ处理，(2)HCIO4水解，(3)LiOH水解，(4)(n-Bu)4Nf处理，和(5)ACoH水解。以大约35%的总收率分离出了完全去保护的孢子毒素羧酸，并与正品进行了鉴定。建立了一种有效地将毒素羧酸2转化为毒素酰胺3的方法。
The total synthesis of palytoxin carboxylic acid and palytoxin amide was achieved from the fully protected palytoxin carboxylic acid. The fully protected palytoxin carboxylic acid 1 contains eight different and 42 total protecting groups. All these protecting groups were successfully removed in five synthetic operations, i.e., (1) DDQ treatment, (2) aqueous HCIO4 hydrolysis, (3) aqueous LiOH hydrolysis, (4) (n-Bu)4NF treatment, and (5) aqueous AcOH hydrolysis. The completely deprotected palytoxin carboxylic acid was isolated in approximately 35% overall yield and identified with the authentic sample. An efficient method to convert palytoxin carboxylic acid 2 into palytoxin amide 3 was developed.