Stereoisomers of Ieodoglucomides A and B: Synthesis and Evaluation of Anticancer Activity

Abstract

Asymmetric total synthesis of α-isomers of ieodoglucomides A and B along with their C14-epimers has been achieved starting from D-glucose. The key reactions involved are α-glycosylation and Grubbs olefin cross-metathesis. These stereochemical analogues and their β-isomers (natural products) were screened for their effects on cytotoxicity against various cancer cell lines and it was found that a few analogues are active relative to the natural ieodoglucomides.

Divinylcarbinol Desymmetrization Strategy: A Concise and Reliable Approach to Chiral Hydroxylated Fatty Acid Derivatives

“…To prove the concept, we initially applied our strategy to a concise synthesis of ( R )- 2 (Scheme ). SAE of divinylcarbinol with (−)-DIPT followed by TBDPS protection of the hydroxyl group afforded the epoxide 12 (≥99% ee). , A cross-metathesis of 12 with 1-nonene provided 13 without undesired olefin isomerization in the presence of 1,4-benzoquinone, and subsequent hydrogenation could afford 14 . Deoxygenation of 14 proceeded effectively with PPh 3 /Zn to give 15 .…”

Chemistry and Biology of Bioactive Glycolipids of Marine Origin

“…In order to identify analogs of ieodoglucomides with improved biological properties, the same authors prepared the α-isomers of ieodoglucomides A and B ( 328 and 329 ) and their C-14-epimers ( 331 and 332 ) ( Scheme 25 ) [ 126 ]. As described in Scheme 25 , the syntheses of these analogues were accomplished according to the same synthetic strategy employed for the synthesis of the natural products, starting from the α-anomer 325 for the synthesis of the analogues 328 and 329 , and from the epimer 330 for the syntheses of the analogues 331 and 332 .…”

Structure and Reactivity of Glycosyl Isocyanides

“…[9,10] Thus, MCRs can be a really valuable tool towards that direction; they could enable a rapid and diverse incorporation of sugar isocyanides into drug-like scaffolds. [11][12][13][14][15][16][17][18][19][20][21][22][23] Recent exciting applications of such glyco-MCR products include antiaging cosmetic preparations. [24] In continuation of our own studies on the glyco-IMCR, [25] besides D-glucose and L-arabinose, we investigate here our established strategy not only on important monosaccharides as D-galactose and D-ribose, but also on disaccharides as D-lactose and even trisaccharides such as α-D-maltotriose.…”