Phosphonoxins III: Synthesis of α-Aminophosphonate Analogs of Antifungal Polyoxins with Anti-Giardia Activity

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• 作者：Michael Staake ; Jay Chauhan ; Ding Zhou ; Aaron Shanker ; Atasi De Chatterjee ; Siddhartha Das ; Steven E. Patterson
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：October 15, 2010
• 年：2010
• 卷：12
• 期：20
• 页码：4596-4599
• 全文大小：302K
• 年卷期：v.12,no.20(October 15, 2010)
• ISSN：1523-7052

文摘

A synthesis of α-aminophosphonate analogs of polyoxins, termed phosphonoxin C1, C2, and C3, has been achieved. The key step was the addition of lithium dimethyl phosphite to the aldehyde of a protected threose derivative. α-Hydroxyphosphonate analogs C4 and C5 were also obtained by taking advantage of an unprecedented conversion of an azide to hydroxyl during treatment with hydrogen on palladium on carbon. The resulting phosphonoxin C5 inhibited the growth of an intestinal protozoan, Giardia lamblia, at low micromolar concentration.