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One‐Step Synthesis of Natural Product‐Inspired Biaryl Ether‐Cyclopeptoid Macrocycles by Double Ugi Multiple‐Component Reactions of Bifunctional Building Blocks
Author(s) -
Michalik Dirk,
Schaks Angela,
Wessjohann Ludger A.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600354
Subject(s) - chemistry , bifunctional , natural product , ether , combinatorial chemistry , component (thermodynamics) , stereochemistry , total synthesis , organic chemistry , catalysis , physics , thermodynamics
Isonitrile‐functionalized biaryl ethers can serve as key building blocks for the highly efficient one‐step production of natural product inspired‐macrocycles, with six or even twelve new bonds and rings with up to 50 members being formed in total yields of up to 51 %. Aliphatic diamine and diacid tethers give access to two different classes of N ‐substituted biaryl ether cyclopeptides, suitable for library construction. As part of a conceptual work on MiBs ( m ultiple m ulticomponent m acrocyclizations/ m acrocycles i ncluding b ifunctional b uilding b locks), the influence of length and type of flexible tethers on the propensity for cyclization is studied.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)