Synonyms:AmphidinolideG; Amphidinolide G1
The research focuses on the total synthesis of Amphidinolide H and G, complex macrolides derived from Dinoflagellates of the genus Amphidinium, which exhibit significant cytotoxicity against human epidermoid carcinoma cells. The synthesis process involved meticulous planning and optimization of the assembly sequence and protecting-group regime. The researchers dissected Amphidinolide H into four building blocks, which were combined through esterification, aldol reaction, metal-catalyzed cross-coupling, and olefin metathesis. Key reactants included Roche ester, itaconic acid monoester, and (S)-citronellal, among others, which were subjected to a series of transformations such as epoxidation, reduction, silylation, and oxidation. The synthesis required innovative strategies, like modified Stille coupling under chloride-free conditions and the application of the Grubbs catalyst for macrocyclization. The success of the synthesis was confirmed through analytical and spectroscopic analyses, which matched the published data for Amphidinolide H and G.
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