Concise Stereocontrolled Synthesis of an α-Carbagalactose Segment of RCAI-56, a Candidate Anticancer Agent

Ushida, Naoki; Nagai, Nobukazu; Adachi, Masaatsu; Nishikawa, Toshio

doi:10.1055/s-0037-1611806

Cited by 1 publication

(1 citation statement)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first synthesis of RCAI-56 involved the preparation of α-carbagalactose 48 in 13 steps from methyl-αd-galactoside, and its reaction with phytosphingosine sulfamidate 49 as the key step for building the KRN7000 scaffold (Scheme 5A). [147] In 2019, Ushida et al [148] have achieved a more concise preparation of 48, involving a key enantioselective Diels-Alder reaction between acrolein and 1-benzyloxy-1,3butadiene, catalyzed by MacMillan imidazolidinone organocatalyst. Direct oxidation of the reaction product 51, followed by bromo-lactonization afforded lactone 52 in 26 % yield over three steps with 91 % ee.…”

Section: Ring Oxygen Replacement Analogsmentioning

confidence: 99%

Chemical Biology of αGalCer: A Chemist's Toolbox for the Stimulation of Invariant Natural Killer T (iNKT) Cells

Romanò

Clausen

2022

Eur J Org Chem

View full text Add to dashboard Cite

Often referred to as the “Swiss Army knife” of the immune system, invariant natural killer T (iNKT) cells are a subpopulation of T lymphocytes stimulated by the synthetic glycolipid α‐galactosylceramide (αGalCer) when in complex with the CD1d receptor of antigen presenting cells. Through their ability to produce TH1 and TH2 cytokines and co‐stimulate several other lymphocytes, iNKT cells have emerged as central players in directing the immune response in a range of physiological processes, such as infections, autoimmune diseases, and cancer. Over the years, synthetic chemistry has advanced the field of iNKT cell stimulation with the development of more efficient approaches to prepare αGalCer, and, additionally, with the chemical synthesis of αGalCer analogs in the search of better TH1/TH2 cytokine skewing compounds for therapeutic applications. Here, we review the strategies for the synthesis of αGalCer and its analogs, including synthetic probes, together with the most important advances in the understanding of the mechanism of action of these compounds, as a guide to the available tools for interrogating the iNKT cell−αGalCer−CD1d complex and inspiration for future research.

show abstract

Section: Ring Oxygen Replacement Analogsmentioning

confidence: 99%