期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 29, 期 34, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202300941
关键词
natural products; atropisomerism; total synthesis; building block; density functional calculations
This article describes the enantioselective synthesis of a chiral 2,2'-biphenol building block and demonstrates its potential for the synthesis of natural products.
A variety of biaryl polyketides exhibit remarkable bioactivities. However, their synthetic accessibility is often challenging. Herein, the enantioselective preparation and synthetic application of an axially chiral 2,2'-biphenol building block is outlined that represents a common motif of these intriguing natural products. Based on the highly regioselective and scalable bromination of a phenol precursor, a coupling process by Lipshutz cuprate oxidation was developed. A copper-mediated deracemization strategy proved to be superior to derivatization or kinetic resolution approaches. Key steps in the overall building block synthesis were rationalized through DFT studies. Utilizing the 2,2'-biphenol, a highly diastereoselective five step synthesis of formerly unknown (+)-di-epi-gonytolide A was developed, thus showcasing the building block's general potential for the synthesis of natural products and their derivatives. En route, the first enantioselective construction of a chromone dimer intermediate was established.
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