Total synthesis of incednam, the aglycon of incednine

Takashi Ohtani, Shinya Tsukamoto, Hiroshi Kanda, Kensuke Misawa, Yoshifumi Urakawa, Takahiro Fujimaki, Masaya Imoto, Yoshikazu Takahashi, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The first total synthesis of incednam (1), the aglycon of antibiotic incednine (2), is described. Incednine has been reported to exhibit significant inhibitory activity against the antiapoptotic oncoproteins Bcl-2 and Bcl-xL. The synthesis of 1 commenced with the preparation of the C1-C13 subunit 3 and the C14-C23 subunit 4. The construction of the novel 24-membered macrocycle was achieved by the application of a Stille coupling between 3 and 4, followed by macrolactamization.

Original languageEnglish
Pages (from-to)5068-5071
Number of pages4
JournalOrganic Letters
Volume12
Issue number21
DOIs
Publication statusPublished - 2010 Nov 5

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antibiotics
Oncogene Proteins
synthesis
Anti-Bacterial Agents
preparation
incednine
incednam

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Ohtani, T., Tsukamoto, S., Kanda, H., Misawa, K., Urakawa, Y., Fujimaki, T., ... Toshima, K. (2010). Total synthesis of incednam, the aglycon of incednine. Organic Letters, 12(21), 5068-5071. https://doi.org/10.1021/ol102400c

Total synthesis of incednam, the aglycon of incednine. / Ohtani, Takashi; Tsukamoto, Shinya; Kanda, Hiroshi; Misawa, Kensuke; Urakawa, Yoshifumi; Fujimaki, Takahiro; Imoto, Masaya; Takahashi, Yoshikazu; Takahashi, Daisuke; Toshima, Kazunobu.

In: Organic Letters, Vol. 12, No. 21, 05.11.2010, p. 5068-5071.

Research output: Contribution to journalArticle

Ohtani, T, Tsukamoto, S, Kanda, H, Misawa, K, Urakawa, Y, Fujimaki, T, Imoto, M, Takahashi, Y, Takahashi, D & Toshima, K 2010, 'Total synthesis of incednam, the aglycon of incednine', Organic Letters, vol. 12, no. 21, pp. 5068-5071. https://doi.org/10.1021/ol102400c
Ohtani T, Tsukamoto S, Kanda H, Misawa K, Urakawa Y, Fujimaki T et al. Total synthesis of incednam, the aglycon of incednine. Organic Letters. 2010 Nov 5;12(21):5068-5071. https://doi.org/10.1021/ol102400c
Ohtani, Takashi ; Tsukamoto, Shinya ; Kanda, Hiroshi ; Misawa, Kensuke ; Urakawa, Yoshifumi ; Fujimaki, Takahiro ; Imoto, Masaya ; Takahashi, Yoshikazu ; Takahashi, Daisuke ; Toshima, Kazunobu. / Total synthesis of incednam, the aglycon of incednine. In: Organic Letters. 2010 ; Vol. 12, No. 21. pp. 5068-5071.
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