Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker.
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.
Chang
Yi-Fan
YF
The Genomics Research Center, Academia Sinica, Nankang, Taipei, 115, Taiwan.
Liu
Chen-Yu
CY
Guo
Chih-Wei
CW
Wang
Yen-Chih
YC
Fang
Jim-Min
JM
Cheng
Wei-Chieh
WC
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*
D045782:Hemiterpenes; D000439:Pentanols; D011108:Polymers; D013450:Sulfones; C009034:prenol