Chang, Yi-FanYi-FanChangCHEN-YU LIUGuo, Chih-WeiChih-WeiGuoWang, Yen-ChihYen-ChihWangFang, Jim-MinJim-MinFangCheng, Wei-ChiehWei-ChiehCheng2022-03-242022-03-242008-09-190022-3263https://scholars.lib.ntu.edu.tw/handle/123456789/602088Solid-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.enSODIUM BENZENESULFINATE; ALLYLIC SULFONES; LIPID-II; STEREOSPECIFIC SYNTHESIS; COMPREHENSIVE SURVEY; PLANT POLYPRENOLS; DOLICHOL; PEPTIDE; PHOSPHORYLATION; ALKYLATIONjournal article10.1021/jo8010182187071722-s2.0-52449127172WOS:000259195200079https://scholars.lib.ntu.edu.tw/handle/123456789/339796https://www.scopus.com/inward/record.uri?eid=2-s2.0-52449127172&doi=10.1021%2fjo8010182&partnerID=40&md5=1a6189312e9d14228ad8cc9d602a23f5