title: Concise synthesis of calystegines B2 and B3via intramolecular Nozaki-Hiyama-Kishi reaction.
abstract: The key step in the concise syntheses of calystegine B2 and its C-2 epimer calystegine B3 was the construction of cycloheptanone 8via an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction of 9, an aldehyde containing a Z-vinyl iodide. Vinyl iodide 9 was obtained by the Stork olefination of aldehyde 10, derived from carbohydrate starting materials. Calystegines B2 (3) and B3 (4) were synthesized from d-xylose and l-arabinose derivatives respectively in 11 steps in excellent overall yields (27% and 19%).
authors.affiliation: Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. yucy@iccas.ac.cn.
authors.forename: Hong-Yao
authors.initials: HY
authors.lastname: Wang
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Kyoko
authors.initials: K
authors.lastname: Kinami
authors.forename: Yi-Xian
authors.initials: YX
authors.lastname: Li
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003508:Cycloheptanes / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D009662:Nortropanes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D003508:Cycloheptanes; D004791:Enzyme Inhibitors; D009662:Nortropanes; D012991:Solanaceous Alkaloids; C095613:calystegine B(2); D006026:Glycoside Hydrolases