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Issue 14, 2005
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New approaches towards the synthesis of the side-chain of mycolactones A and B

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Abstract

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 sp2–sp2 coupling between C7′ and C8′ or C9′ and C10′ (Fig. 1) were also explored.

Graphical abstract: New approaches towards the synthesis of the side-chain of mycolactones A and B

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Article information


Submitted
28 Apr 2005
Accepted
20 May 2005
First published
15 Jun 2005

Org. Biomol. Chem., 2005,3, 2524-2533
Article type
Paper

New approaches towards the synthesis of the side-chain of mycolactones A and B

R. P. van Summeren, B. L. Feringa and A. J. Minnaard, Org. Biomol. Chem., 2005, 3, 2524
DOI: 10.1039/B505980A

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