期刊
NATURE CATALYSIS
卷 2, 期 10, 页码 925-930出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/s41929-019-0345-0
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资金
- Swiss National Science Foundation [BSSGI0-155902/1]
- University of Basel
- NCCR Molecular Systems Engineering
- Swiss National Science Foundation (SNF) [BSSGI0_155902] Funding Source: Swiss National Science Foundation (SNF)
The cyclization of poly-beta-carbonyl-substrates controlled by polyketide synthases intricately governs the biosynthesis of a wide range of aromatic polyketides. Analogous small-molecule-catalysed processes would conceivably induce selective cyclizations of non-canonical polycarbonyl substrates to provide products distinct from natural polyketides. Here, we report a secondary amine-catalysed twofold cyclization of non-canonical hexacarbonyl substrates, furnishing enantioenriched tetra-ortho-substituted binaphthalenes. The substrates were prepared by a fourfold ozonolysis of dicinnamyl biindenes and converted under catalyst control with high atroposelectivity. Privileged catalysts, helicenes and ligands are readily accessible from the binaphthalene products stemming from the non-canonical polyketide cyclizations.
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