title: An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (-)-hapalosin.
abstract: A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1= TBS, P2= H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. bgwei1974@fudan.edu.cn.
authors.forename: Chang-Mei
authors.initials: CM
authors.lastname: Si
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. bgwei1974@fudan.edu.cn.
authors.forename: Lu-Ping
authors.initials: LP
authors.lastname: Shao
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. bgwei1974@fudan.edu.cn and Institutes of Biomedical Sciences, Fudan University, 130 Dongan Road, Shanghai 200032, China.
authors.forename: Zhuo-Ya
authors.initials: ZY
authors.lastname: Mao
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. bgwei1974@fudan.edu.cn.
authors.forename: Wen
authors.initials: W
authors.lastname: Zhou
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. bgwei1974@fudan.edu.cn and Institutes of Biomedical Sciences, Fudan University, 130 Dongan Road, Shanghai 200032, China.
authors.forename: Bang-Guo
authors.identifier: http://orcid.org/0000-0002-8870-2597
authors.initials: BG
authors.lastname: Wei
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D047630:Depsipeptides; D007769:Lactams; D007783:Lactones; D011760:Pyrrolidinones; C058280:preussin; C111358:hapalosin; D000841:Anisomycin; C028537:2-pyrrolidone; C013165:statine