Total Syntheses of C60- and C100-Dolichols
- 30 July 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (17), 11549-11559
- https://doi.org/10.1021/acs.joc.0c01327
Abstract
C60- and C100-dolichols were synthesized. Z-Selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of Z-isoprene unit. Isoprene chain was efficiently elongated by an SN2-type coupling between allyl sulfone and allyl chloride using t-BuOK. These key reactions enabled the efficient syntheses of dolichols. This study will pave the way for the functional studies of dolichols.Keywords
Funding Information
- Japan Society for the Promotion of Science (15H05836, 16H01885, 16H05924, 18H03934, 19KK0145, 20H00404, 20H04709, 20K05727)
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