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

doi:10.1021/ol102400c

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

応用化学科

研究成果: Article › 査読

19 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	5068-5071
ページ数	4
ジャーナル	Organic Letters
巻	12
号	21
DOI	https://doi.org/10.1021/ol102400c
出版ステータス	Published - 2010 11月 5

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol102400c

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title = "Total synthesis of incednam, the aglycon of incednine",

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.",

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

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T1 - Total synthesis of incednam, the aglycon of incednine

AU - Ohtani, Takashi

AU - Tsukamoto, Shinya

AU - Kanda, Hiroshi

AU - Misawa, Kensuke

AU - Urakawa, Yoshifumi

AU - Fujimaki, Takahiro

AU - Imoto, Masaya

AU - Takahashi, Yoshikazu

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

PY - 2010/11/5

Y1 - 2010/11/5

N2 - 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.

AB - 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.

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DO - 10.1021/ol102400c

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Total synthesis of incednam, the aglycon of incednine

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