Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker
Journal
The Journal of Organic Chemistry
Journal Volume
73
Journal Issue
18
Pages
7197
Date Issued
2008-09-19
Author(s)
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.
Subjects
SODIUM BENZENESULFINATE; ALLYLIC SULFONES; LIPID-II; STEREOSPECIFIC SYNTHESIS; COMPREHENSIVE SURVEY; PLANT POLYPRENOLS; DOLICHOL; PEPTIDE; PHOSPHORYLATION; ALKYLATION
Publisher
AMER CHEMICAL SOC
Type
journal article