通过(3 + 2)环加成实现复杂四环稠合骨架的合成

Porte Vincent, van Veen Branca C, Zhang Haoqi, Piacentini Paolo, Matheu Sergio Armentia, Woolford Sophie, Sokol Kevin R, Shaaban Saad, Weinstabl Harald, Maulide Nuno

Christian Doppler Laboratory for Entropy-Oriented Drug Design, Institute of Organic Chemistry, University of Vienna, 1090 Vienna, Austria.

Boehringer Ingelheim RCV GmbH&CoKG, 1120 Vienna, Austria.

Org Lett. 2024 Jun 14;26(23):4873-4876. doi: 10.1021/acs.orglett.4c01269. Epub 2024 May 31.

We describe the single-step formation of complex tetracyclic fused scaffolds enabled by (3 + 2) cycloaddition of azomethine ylides. Various indoles, N-protecting groups, and amino acids are well tolerated. The products are obtained in a catalyst-free manner with moderate to excellent yield and high diastereoselectivity. Representing a new scaffold that is not yet found in nature, the construction of pyrrolidine-fused cyclohepta-, azepino-, or oxepinoindoles could be found valuable in the synthesis of new pseudo-natural products.

我们描述了通过甲亚胺叶立德的(3 + 2)环加成实现的复杂四环稠合支架的一步形成。各种吲哚、N-保护基团和氨基酸都具有良好的耐受性。产物以无催化剂的方式获得，产率中等至优异，非对映选择性高。作为一种尚未在自然界中发现的新支架，吡咯烷稠合的环庚并、氮杂环庚并或氧杂环庚并吲哚的构建在新型拟天然产物的合成中可能具有重要价值。