Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 34, Pages 10523-10534Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000924
Keywords
antibiotics; biaryls; cross-coupling; macrocycles; natural products
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Funding
- CNRS
- Centre de Recherche de Gif, ICSN
- ICSN
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Development of the total syntheses of arylomycins A(1) and B-2 is detailed. Key features of our approach include 1) formation of 14-membered meta,meta-cyclophane by an intramolecular Suzuki-Miyaura reaction; 2) incorporation of N-Me-4-hydroxyphenylglycine into the cyclization precursor, which avoids the late-stage low-yielding N-methylation step; 3) segment coupling of a fully elaborated peptide side chain to the macrocycle, which makes the synthesis highly convergent. Overall, arylomycin A(2) was obtained in 13 steps from L-Tyr for the longest linear sequence, in 13% overall yield. Arylomycin B-2 was synthesized in 10 steps from L-3-nitro-Tyr, in 10% overall yield.
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