Total Syntheses of C60- and C100-Dolichols.

J Org Chem

Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan.

Published: September 2020

C60- and C100-dolichols were synthesized. A -selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of the -isoprene unit. An isoprene chain was efficiently elongated by an S2-type coupling between allyl sulfone and allyl chloride using -BuOK. These key reactions enabled the efficient syntheses of dolichols. This study will pave the way for the functional studies of dolichols.

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http://dx.doi.org/10.1021/acs.joc.0c01327DOI Listing

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