Total Syntheses of C60- and C100-Dolichols

Total Syntheses of C60- and C100-Dolichols

C60- and C100-dolichols were synthesized. A Z-selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of the Z-isoprene unit. An isoprene chain was efficiently elongated by an SN2-type coupling between allyl sulfone and allyl chloride using t...

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Veröffentlicht in:Journal of organic chemistry 2020-09, Vol.85 (17), p.11549-11559
Hauptverfasser: Hirao, Kohtaro, Ono, Risako, Manabe, Yoshiyuki, Masui, Seiji, Atomi, Haruyuki, Fukase, Koichi
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Zusammenfassung:C60- and C100-dolichols were synthesized. A Z-selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of the Z-isoprene unit. An 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01327