Total Synthesis of Tambromycin Enabled by Indole C–H
Functionalization
Posted on 2018-03-27 - 18:48
The total synthesis of tambromycin
(1), a recently
isolated tetrapeptide, is reported. This unusual natural product possesses
a highly modified tryptophan-derived indole fragment fused to an α-methylserine-derived
oxazoline ring, and a unique noncanonical amino acid residue named
tambroline (11). A convergent synthesis of tambromycin
was achieved by a 13-step route that leveraged recent developments
in the field of C–H functionalization to prepare the complex
indole fragment, as well as an efficient synthesis of tambroline that
featured a diastereoselective amination of homoproline.
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Miley, Galen P.; Rote, Jennifer C.; Silverman, Richard B.; Kelleher, Neil L.; Thomson, Regan J. (2018). Total Synthesis of Tambromycin Enabled by Indole C–H
Functionalization. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b00700