Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Heterocycles called The paecilin puzzle – enantioselective synthesis of the proposed structures of paecilin A and B, Author is Tietze, Lutz F.; Ma, Ling; Jackenkroll, Stefan; Reiner, Johannes R.; Hierold, Judith; Gnanaprakasam, Boopathy; Heidemann, Sven, which mentions a compound: 138984-26-6, SMILESS is C12=O[Rh+2]3(O=C4[N-]5CCCCC4)([N-]6C(CCCCC6)=O7)[N-](CCCCC8)C8=O[Rh+2]357[N-]1CCCCC2, Molecular C24H40N4O4Rh2, SDS of cas: 138984-26-6.
For the synthesis of diastereomers of paecilin A and paecilin B, a phenol derivative containing an alkene group was treated with Pd(II) in the presence of the chiral BOXAX ligands. The synthesis of the target compounds was achieved using (4S,4’S)-2,2′-[1,1′-binaphthalene]-2,2′-diylbis[4,5-dihydro-4-(phenylmethyl)oxazole] (4S,4’S)-2,2′-[[1,1′-binaphthalene]-2,2′-diyl]bis[4,5-dihydro-4-(1-methylethyl)oxazole] as catalysts. A subsequent Sharpless dihydroxylation afforded two isomeric diols, which were further transformed into 31 and 32. The final steps included removal of the silyl protecting group with simultaneous lactone formation, oxidation and cleavage of the Me ether. For the preparation of the dimeric paecilin A brominated intermediate 38 was treated with (Bpin)2, S-Phos and Pd(OAc)2. The spectroscopic data of the new compounds [i.e.. (hydroxy)[(oxo)furanyl](oxo)benzopyrancarboxylic acid ester diastereomers] did not match those of the isolated natural products [i.e., 3,3′,4,4′-tetrahydro-5,5′-dihydroxy-4,4′-dioxo-2,2′-bis(tetrahydro-3-methyl-5-oxo-2-furanyl)[8,8′-bi-2H-1-benzopyran]-2,2′-dicarboxylic acid 2,2′-dimethyl ester (paecilin A) and (2R)-3,4-dihydro-5-hydroxy-4-oxo-2-[(2S,3S)-tetrahydro-3-methyl-5-oxo-2-furanyl]-2H-1-benzopyran-2-carboxylic acid (paecilin B) ].
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