title: The total synthesis of D-chalcose and its C-3 epimer.
abstract: We completed a new and efficient synthesis of D-chalcose (I) and the first synthesis of its C-3 epimer (I') in nine steps with overall yields of 23% and 24%, respectively. The key steps in the sequence were the formation of the stereocenter on C3 via Grignard reaction, the introduction of the stereogenic center on C2 by Sharpless asymmetric dihydroxylation, the protection of the C1 and C2 hydroxy groups with tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf), and the selective cleavage of the primary OTBS ether using catalytic DL-10-camphorsulfonic acid (CSA) in MeOH.
authors.affiliation: Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Sun
authors.affiliation: Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Song
authors.initials: S
authors.lastname: Fan
authors.affiliation: Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Zhan
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Guoning
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Center for Molecular Imaging, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, MA 02215, United States.
authors.forename: Kai
authors.initials: K
authors.lastname: Bao
authors.affiliation: Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Weige
authors.initials: W
authors.lastname: Zhang
keywords: asymmetric dihydroxylation; chalcose; epimer; total synthesis