Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 14, 2005
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Publication details

The article was received on 28 Apr 2005, accepted on 20 May 2005 and first published on 15 Jun 2005


Article type: Paper
DOI: 10.1039/B505980A
Citation: Org. Biomol. Chem., 2005,3, 2524-2533

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements