Issue 43, 2023

Synthesis of the diazatricycloundecane scaffold via gold(i)-catalysed Conia-ene-type 5-exo-dig cyclization and stepwise substituent assembly for the construction of an sp3-rich compound library

Abstract

The bridged diazatricycloundecane sp3-rich scaffold was synthesised via the gold(I)-catalysed Conia-ene reaction. The electron-donating property of the siloxymethyl group on alkyne 1 enabled 6-endo-dig cyclization, whereas the ethoxy carbonyl group on alkyne 4 led to 5-exo-dig cyclization with complete regioselectivity in the Conia-ene reaction. The resulting bridged diazatricycloundecane scaffold 5 allowed the construction of a library of sp3-rich compounds. Among the compounds synthesised, compounds 6e and 6f inhibited the hypoxia inducible factor 1 (HIF-1) downstream signaling pathway without affecting HIF-1α mRNA expression.

Graphical abstract: Synthesis of the diazatricycloundecane scaffold via gold(i)-catalysed Conia-ene-type 5-exo-dig cyclization and stepwise substituent assembly for the construction of an sp3-rich compound library

Supplementary files

Article information

Article type
Paper
Submitted
23 Sep 2023
Accepted
14 Oct 2023
First published
16 Oct 2023

Org. Biomol. Chem., 2023,21, 8716-8726

Synthesis of the diazatricycloundecane scaffold via gold(I)-catalysed Conia-ene-type 5-exo-dig cyclization and stepwise substituent assembly for the construction of an sp3-rich compound library

T. Doi, K. Umedera, K. Miura, T. Morita and H. Nakamura, Org. Biomol. Chem., 2023, 21, 8716 DOI: 10.1039/D3OB01534C

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