Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker

The Journal of Organic Chemistry
Yi-Fan ChangWei-Chieh Cheng

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.

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Citations

Jul 31, 2013·ACS Combinatorial Science·Yi-Wen PanWei-Chieh Cheng
Aug 7, 2012·Journal of the American Chemical Society·Dusan HesekShahriar Mobashery
Nov 16, 2017·Chemical Communications : Chem Comm·Mijoon LeeShahriar Mobashery
Mar 31, 2015·Chemistry : a European Journal·Cheng-Kun LinWei-Chieh Cheng
Feb 11, 2014·European Journal of Organic Chemistry·Baolin WuPeng George Wang
Feb 10, 2009·Journal of Combinatorial Chemistry·Hao-Wei ShihWei-Chieh Cheng
Jul 15, 2021·Proceedings of the National Academy of Sciences of the United States of America·Rong ChenTiangang Liu
Oct 18, 2013·Journal of the American Chemical Society·Shih-Hsien HuangChi-Huey Wong
Jan 1, 2014·Journal of the American Chemical Society·Feng LiuBenjamin G Davis

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