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Total Synthesis and Structure Confirmation of Fusaroside

“…LN-11 from the leaves of Melia azedarach, was isolated in 2012 by Gao and co-workers, and its structure was proposed as 1 (Figure ). Fusaroside is the first example of the novel class of natural glycolipids, having an unusual branched fatty acyl chain linked to the C4–OH of the trehalose unit . As per the proposed structure, the long-chain fatty acyl moiety contains a conjugated β-ketoester functionality having a geminal dimethyl substituent at the C2 position of the ester, a conjugated diene at C11 and C13, and an isolated double bond at C18.…”

“…1 Fusaroside is the first example of the novel class of natural glycolipids, having an unusual branched fatty acyl chain linked to the C4− OH of the trehalose unit. 2 As per the proposed structure, the long-chain fatty acyl moiety contains a conjugated β-ketoester functionality having a geminal dimethyl substituent at the C2 position of the ester, a conjugated diene at C11 and C13, and an isolated double bond at C18. Due to our long-standing interest in the chemical synthesis of trehalose-containing glycolipids and oligosaccharides, 3−9 fusaroside 1 attracted our immediate attention and eventually we were successful in synthesizing the molecule.…”