title: Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core structure of tagetitoxin.
abstract: Tagetitoxin is an unusually densely functionalized natural product, consisting of an unprecedented oxathiabicyclo[3.3.1]nonane ring system possessing acetate, phosphate, amide, carboxylic acid, and amine groups with six contiguous asymmetric centers. A fully functionalized core structure of tagetitoxin was synthesized from tri-O-acetyl-D-galactal in a highly stereoselective manner.
authors.affiliation: Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. nisikawa@agr.nagoya-u.ac.jp.
authors.forename: Hitomi
authors.initials: H
authors.lastname: Yamada
authors.forename: Masaatsu
authors.initials: M
authors.lastname: Adachi
authors.forename: Toshio
authors.initials: T
authors.lastname: Nishikawa
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003998:Dicarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D006900:Hydroxylation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D003998:Dicarboxylic Acids; D009943:Organophosphorus Compounds; C458301:bicyclo(3.3.1)nonane; C002038:galactal; C062221:tagetitoxin; D005690:Galactose