Synthesis of a Phosphonate Analog of Sialic Acid (Neu5Ac) Using Indium-Mediated Allylation of Unprotected Carbohydrates in Aqueous Media

Synthesis of a Phosphonate Analog of Sialic Acid (NeuSAc) Using Indium-Mediated Allylation of Unprotected Carbohydrates in Aqueous Media

[Development of unprotected syntheses in aqueous media].

Introduction of carbon side chain at C(3)-position of indole ring was accomplished by using Pd-catalyzed allylation and vinylation. The selective vinylation at C(3)-position of 4-bromoindole was applied to the synthesis of optically active 4-bromotryptophan derivatives, which was used as a starting material for the synthesis of several optically active ergot alkaloids, which were clavicipitic a...

Total synthesis of antillatoxin.

The total synthesis of natural (4R,5R)-antillatoxin and its analog (4S,5S)-antillatoxin has been achieved; the optically pure key intermediates were prepared from indium mediated allylation of either primary or secondary allylic bromide with aldehyde in aquoues media, followed by highly selective Luche's reduction and chiral resolution.

Indium - mediated Allylation of α - Imino Esters in Aqueous Media

Targeting aberrant sialylation in cancer cells using a fluorinated sialic acid analog impairs adhesion, migration, and in vivo tumor growth.

Cancer cells decorate their surface with a dense layer of sialylated glycans by upregulating the expression of sialyltransferases and other glycogenes. Although sialic acids play a vital role in many biologic processes, hypersialylation in particular has been shown to contribute to cancer cell progression and metastasis. Accordingly, selective strategies to interfere with sialic acid synthesis ...