Total Synthesis of Myrmekioside A, a Mono‐O‐alkyl‐diglycosylglycerol from Marine Sponge Myrmekioderma sp. Issue 19 (28th May 2015)

• Record Type: Journal Article
• Authors: Zhang, Jun; Li, Chunxia; Sun, Linlin; Yu, Guangli; Guan, Huashi
• Is Part Of: European journal of organic chemistry. Issue 19(2015)
• Page Start: 4246
• Page End: 4253
• Publication Date: 2015-05-28
• Subjects: Total synthesis -- Natural products -- Carbohydrates -- Glycosides -- Glycosylation -- Glycolipids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500471
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Myrmekioside A, which was isolated from the marine sponge Myrmekioderma sp. as a member of the family of natural mono‐ O ‐alkyl‐diglycosylglycerols, and which has a strong reversion effect on the tumor cell morphology of ras‐transformed cells at 5 μg/mL, was synthesized for the first time in 17 steps and 14 % overall yield. The β‐glycosidic linkages in myrmekioside A were successfully constructed by the neighbouring‐group‐participation approach using trichloroacetimidates and thioglycosides as glycosyl donors. The 2 R absolute configuration at C‐2 of the glycerol backbone was derived from ( S )‐1, 2‐isopropylideneglycerol (8 ). This synthetic approach may be applicable to the preparation of other myrmekioside analogues featuring different sugars and alkyl chains for further structure–activity relationship studies. Abstract : Myrmekioside A, a natural mono‐ O ‐alkyl‐diglycosylglycerol from a marine sponge, was synthesized for the first time. The β‐glycosidic linkages were constructed by the neighbouring‐group‐participation approach. This synthetic approach may be applicable to other natural mono‐ O ‐alkyl‐diglycosylglycerols and their structural variants.