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

Research output: Contribution to journal › Article › peer-review

19 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 language	English
Pages (from-to)	5068-5071
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	21
DOIs	https://doi.org/10.1021/ol102400c
Publication status	Published - 2010 Nov 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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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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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Total synthesis of incednam, the aglycon of incednine

Abstract

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