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Total Synthesis of Tambromycin Enabled by Indole C-H Functionalization.

ABSTRACT: 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 ?-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.

SUBMITTER: Miley GP

PROVIDER: S-EPMC5953429 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Total Synthesis of Tambromycin Enabled by Indole C-H Functionalization.

Miley Galen P GP Rote Jennifer C JC Silverman Richard B RB Kelleher Neil L NL Thomson Regan J RJ

Organic letters 20180327 8

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 effic ...[more]

PMID: 29584440

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