Sulfone-mediated syntheses of crocetin derivatives: regioselectivity of highly functionalized building blocks.
New C5 sulfone building blocks containing a masked polar end group have been devised for the efficient synthesis of carotenoids with polar termini. Chemoselectivity or the regiochemical issue of the highly functionalized units has been carefully addressed depending on the soft or hard nature of electrophiles. These building blocks have been successfully applied to the syntheses of crocetin derivatives, crocetin dial and the novel crocetin dinitrile.
Department of Nano Science and Engineering, ‡Department of Energy and Biotechnology, and §Department of Chemistry, Myong Ji University , Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 449-728, Korea.
Eun-Taek
ET
Oh
Young-Hun
YH
Kim
Jingquan
J
Jin
Liang
L
Su
Jung-Ah
JA
Seo
Sangho
S
Koo
D002338:Carotenoids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*; D014801:Vitamin A / Q000031:analogs & derivatives
D009570:Nitriles; D013450:Sulfones; C487773:trans-sodium crocetinate; D014801:Vitamin A; D002338:Carotenoids