1407975-89-6

Upstream product

• 1195788-06-7 C₄₃H₇₆O₉Si₃ 
• 1195787-98-4 (2R,3S,4R,6R)-6-[(1R)-2-benzyloxy-1-(tert-butyldimethylsilyloxy)-ethyl]-3,4-bis-(tertbutyldimethylsilyloxy)-2-[(1R,2R)-1,2-bis-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)propyl]-tetrahydropyran 

Downstream Products

• 1407975-90-9 C₁₈H₂₈O₉ 
• 1436406-56-2 C₅₄H₁₁₂O₉Si₆ 

Relevant academic research and scientific papers

Synthesis and structure revision of the C43-C67 part of amphidinol 3

Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of AM3 was revised from R to S.

Confirmation of the absolute configuration at C45 of amphidinol 3

Amphidinol 3 (AM3), a membrane-active agent isolated from the dinoflagellate Amphidinium klebsii, consists of a long carbon chain containing 25 stereogenic centers. Although the absolute configuration of AM3 was determined by extensive NMR analysis and degradation of the natural product, the partial structure corresponding to the tetrahydropyran ring system was found to be antipodal to that of karlotoxin 2, a structurally related compound recently isolated from the dinoflagellate Karlodinium veneficum. By extensive degradation of the natural product and conversion of the resulting alcohol to an MTPA ester, the absolute configuration at C45 of AM3 was confirmed to be R, supporting the originally proposed structure.