Direct Biomimetic Synthesis of β‑Carboline Alkaloids from Two Amino Acids

The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of β-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a gre...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 19; pp. 12247 - 12254
Main Authors Wang, Zi-Xuan, Xiang, Jia-Chen, Cheng, Yan, Ma, Jin-Tian, Wu, Yan-Dong, Wu, An-Xin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.10.2018
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Biomimetics
Carbolines - chemistry
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Organic
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoisomerism
Tryptophan - chemistry
TUNICATE EUDISTOMA-OLIVACEUM
ASSISTED SYNTHESIS
ANTITUMOR AGENTS
REAGENT
ORGANIC-SYNTHESIS
NATURAL-PRODUCTS
ANTI-HIV
ALPHA
DERIVATIVES
METHYL KETONES
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Summary:The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of β-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet–Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01668