title: Merremoside D: de novo synthesis of the purported structure, NMR analysis, and comparison of spectral data.
abstract: The first synthesis of the purported structure of Merremoside D has been achieved in 22 longest linear steps. The de novo asymmetric synthesis relied on the use of asymmetric catalysis to selectively install all 21 stereocenters in the final compounds from commercially available achiral starting materials. Adiabatic gradient 2D NMR techniques (gHSQCAD, gHMBCAD, gH2BCAD, gHSQCTOXYAD, ROESYAD) were used to completely assign the structure of synthetic Merremoside D. Comparison of our assignments with the limited NMR data reported for natural Merremoside D allows for the tentative confirmation of its structure.
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
authors.forename: Ehesan U
authors.initials: EU
authors.lastname: Sharif
authors.forename: Hua-Yu Leo
authors.initials: HY
authors.lastname: Wang
authors.forename: Novruz G
authors.initials: NG
authors.lastname: Akhmedov
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D002384:Catalysis; D027722:Convolvulaceae / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D009844:Oligosaccharides; C057149:merremoside D