title: Synthesis of natural products containing cyclohexane units utilizing the Ferrier carbocyclization reaction.
abstract: The Ferrier carbocyclization reaction is one of the most powerful transformations of carbohydrates. This reaction provides enantiomerically pure cyclohexanone derivatives from aldohexoses, and is particularly useful in the chiral pool synthesis of cyclohexane-containing natural products from carbohydrates. We have investigated the synthesis of natural products utilizing the Ferrier carbocyclization reaction. This account provides a brief overview of the Ferrier carbocyclization and its application to natural product synthesis. The utility and versatility of the Ferrier carbocyclization reaction are showcased with the syntheses of hygromycin A, lycoricidine, actinobolin, galanthamine, and morphine starting from carbohydrates.
authors.affiliation: Department of Applied Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan. chida@applc.keio.ac.jp.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002241:Carbohydrates; D003510:Cyclohexanes; C506365:Cyclohexane
keywords: Ferrier carbocyclization reaction; carbohydrates; chiral pool; natural products; total synthesis