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
  • 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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