title: Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker.
abstract: Solid-phase organic synthesis of polyprenols with a traceless sulfone linker is described. The polymer-bound benezenesulfinate is first linked with the "tail" building blocks of isoprenyl chlorides via S-alkylation. With use of dimsyl anion as an appropriate base, the polymer-bound alpha-sulfonyl carbanion is generated and coupled with other "body" building blocks in an efficient manner. After repeated processes and a global palladium-catalyzed desulfonation with LiEt 3BH as the reducing agent, the desired polyprenols with various chain lengths and geometrical configurations are obtained in 32-59% overall yields. The solid-phase synthesis offers the advantage in facile isolation of polyprenols without tedious operation or time-consuming purification.
authors.affiliation: The Genomics Research Center, Academia Sinica, Nankang, Taipei, 115, Taiwan.
authors.forename: Yi-Fan
authors.initials: YF
authors.lastname: Chang
authors.forename: Chen-Yu
authors.initials: CY
authors.lastname: Liu
authors.forename: Chih-Wei
authors.initials: CW
authors.lastname: Guo
authors.forename: Yen-Chih
authors.initials: YC
authors.lastname: Wang
authors.forename: Jim-Min
authors.initials: JM
authors.lastname: Fang
authors.forename: Wei-Chieh
authors.initials: WC
authors.lastname: Cheng
mesh_terms: D045782:Hemiterpenes; D015394:Molecular Structure; D000439:Pentanols / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D045782:Hemiterpenes; D000439:Pentanols; D011108:Polymers; D013450:Sulfones; C009034:prenol