2. Academic Validation
  3. Total synthesis of sandramycin and its analogues via a multicomponent assemblage

Total synthesis of sandramycin and its analogues via a multicomponent assemblage

  • Org Lett. 2014 Jan 17;16(2):428-31. doi: 10.1021/ol403319m.
Katsushi Katayama 1,  Koji Nakagawa,  Hiroshi Takeda,  Akira Matsuda,  Satoshi Ichikawa
Affiliations

Affiliation

  • 1 Faculty of Pharmaceutical Sciences, Hokkaido University , Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
PMID: 24341513 DOI: 10.1021/ol403319m
Abstract

The total synthesis of sandramycin has been accomplished by using a Staudinger/aza-Wittig/diastereoselective Ugi three-component reaction sequence as a key step to obtain a linear pentadepsipeptide. Subsequent [5 + 5] coupling of the penptapeptide, macrolactamization, and introduction of the quinaldin chromophores afforded sandramycin. Dihydroxy and diacetoxy analogues were also prepared, and the cytotoxic activity of these analogues against a range of human Cancer cell lines was evaluated.

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