title: A carbohydrate-based approach for the total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-Di-epi-dinemasone B.
abstract: (-)-Dinemasone B was isolated by Krohn and co-workers from a culture of the endophytic fungus Dinemasporium strigosum and has shown promising antimicrobial activity. Described herein is the first total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B. Their absolute configurations were also determined. The developed synthesis features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from D-glucose.
authors.affiliation: The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University , Beijing 100191, P. R. China.
authors.forename: Xiaochao
authors.initials: X
authors.lastname: Xue
authors.forename: Zhaojun
authors.initials: Z
authors.lastname: Yin
authors.forename: Xiangbao
authors.initials: X
authors.lastname: Meng
authors.forename: Zhongjun
authors.initials: Z
authors.lastname: Li
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D011753:Pyrones; D013141:Spiro Compounds; C586623:dinemasone B