title: Selective transformations of carbonyl functions in the presence of α,β-unsaturated ketones: concise asymmetric total synthesis of decytospolides A and B.
abstract: Enones selectively react with a combination of PPh(3) and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asymmetric total syntheses of decytospolides A and B.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , Suita, Osaka 565-0871, Japan.
authors.forename: Kenzo
authors.initials: K
authors.lastname: Yahata
authors.forename: Masaki
authors.initials: M
authors.lastname: Minami
authors.forename: Kei
authors.initials: K
authors.lastname: Watanabe
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Fujioka
mesh_terms: D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D007659:Ketones; D017646:Organosilicon Compounds; D011714:Pyrans; C000589853:decytospolide A; C000589854:decytospolide B