title: Synthesis and Determination of Absolute Configuration of Lentztrehalose A.
abstract: The synthesis of lentztrehalose A, a naturally occurring trehalose derivative exhibiting various biological activities including autophagy-inducing activity, was achieved. The synthesis commenced with the selective protection of hydroxyl groups of commercially available trehalose, followed by the introduction of the side chain moiety by two methods: 1) prenylation and successive diastereoselective dihydroxylation; or 2) etherification by opening of the chiral epoxide. The present synthetic study clarified the unreported absolute configuration of the secondary alcohol part in the side chain portion.
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN), Tokyo.
authors.forename: Ming
authors.initials: M
authors.lastname: Zhang
authors.forename: Shun-ichi
authors.initials: S
authors.lastname: Wada
authors.forename: Fuyuki
authors.initials: F
authors.lastname: Amemiya
authors.forename: Takumi
authors.initials: T
authors.lastname: Watanabe
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D039903:Actinobacteria / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry*; D006900:Hydroxylation; D008968:Molecular Conformation; D054876:Prenylation; D013237:Stereoisomerism; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D001688:Biological Products; D014199:Trehalose