Abstract
A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic α-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the α-carboline fragment.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biological Products / chemical synthesis
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Biological Products / chemistry
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Diazonium Compounds / chemistry*
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / chemistry
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Molecular Conformation
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Oligopeptides / chemistry*
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Peptides, Cyclic / chemical synthesis*
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Peptides, Cyclic / chemistry
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Stereoisomerism
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Tryptophan / chemistry*
Substances
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Biological Products
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Diazonium Compounds
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Indole Alkaloids
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Oligopeptides
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Peptides, Cyclic
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chaetominine
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kapakahine B
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kapakahine F
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selectfluor
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Tryptophan