英地那的全合成，英地那宁的苷元。

Total synthesis of incednam, the aglycon of incednine.

机构信息

Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

出版信息

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

DOI:10.1021/ol102400c

PMID:20939604

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.

摘要

本文描述了抗生素 incednine（2）的苷元 incednam（1）的首次全合成。已有报道称，incednine 对抑制抗凋亡癌蛋白 Bcl-2 和 Bcl-xL 具有显著的抑制活性。1 的合成从 C1-C13 亚基 3 和 C14-C23 亚基 4 的制备开始。通过在 3 和 4 之间应用 Stille 偶联，然后进行大环内酯化，构建了新型的 24 元大环。