期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 3, 期 14, 页码 2524-2533出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b505980a
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New approaches towards the synthesis of the C1' - C16' side-chain of mycolactones A and B from Mycobacterium ulcerans are reported. Chiral building block 4 ( Fig. 2) with the correct stereochemistry was obtained starting from naturally occurring monosaccharides, i.e. D-glucose or L-rhamnose. The polyunsaturated moiety 3 was synthesized in only 3 steps from 2,4-dimethylfuran. The building blocks were connected through a Sonogashira coupling resulting in the fast and convergent assembly of an 8,9-dehydro analogue 2 of the side-chain of mycolactones A and B. The synthesis of 1 is at this stage hampered by the lack of a selective partial hydrogenation protocol for alkynes embedded in a conjugated system. Alternative strategies involving palladium catalyzed sp(2) - sp2 coupling between C7' and C8' or C9' and C10' ( Fig. 1) were also explored.
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