2. Academic Validation
  3. Total Synthesis of Tunicamycin V

Total Synthesis of Tunicamycin V

  • Org Lett. 2018 Jan 5;20(1):256-259. doi: 10.1021/acs.orglett.7b03623.
Kazuki Yamamoto 1,  Fumika Yakushiji 1 2,  Takanori Matsumaru 1 2,  Satoshi Ichikawa 1 2
Affiliations

Affiliations

  • 1 Faculty of Pharmaceutical Sciences, Hokkaido University , Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
  • 2 Center for Research and Education on Drug Discovery, Faculty of Pharmaceutical Sciences, Hokkaido University , Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
PMID: 29256622 DOI: 10.1021/acs.orglett.7b03623
Abstract

The total synthesis of tunicamycin V is described. This strategy is based on the initial construction of tunicaminyluracil, which is regarded to play an important role in the observed biological activities. The key to the synthesis was a Mukaiyama aldol reaction followed by a furan-oxidation to construct the undecose skeleton, a [3,3] sigmatropic rearrangement of a cyanate, and a highly selective trehalose-type glycosylation.

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