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. 2010 Nov 5;12(21):5068-71.
doi: 10.1021/ol102400c.

Total synthesis of incednam, the aglycon of incednine

Takashi Ohtani  1 , Shinya Tsukamoto, Hiroshi Kanda, Kensuke Misawa, Yoshifumi Urakawa, Takahiro Fujimaki, Masaya Imoto, Yoshikazu Takahashi, Daisuke Takahashi, Kazunobu Toshima
Affiliations

Total synthesis of incednam, the aglycon of incednine

Takashi Ohtani et al. Org Lett. .

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.

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