Bioinspired Indole Prenylation Reactions in Water
Satomi Tanaka1, Shinya Shiomi1, Hayato Ishikawa1
1Department of Chemistry, Graduate School of Science and Technology, Kumamoto University , 2-39-1, Kurokami, Chuo-ku, Kumamoto 860-8555, Japan.
Abstract:
Isoprene units derived from dimethylallyl diphosphate (DMAPP) are an important motif in many natural products including terpenoids, carotenoids, steroids, and natural rubber. Understanding the chemical characteristics of DMAPP is an important topic in natural products chemistry, organic chemistry, and biochemistry. We have developed a direct bioinspired indole prenylation reaction using DMAPP or its equivalents as the electrophile in homogeneous aqueous acidic media in the absence of enzyme to provide prenylated indole products. After establishing the bioinspired indole prenylation reaction, this was then used to achieve the synthesis of a series of natural products, namely, N-prenylcyclo-l-tryptophyl-l-proline, tryprostatins, rhinocladins, and terezine D.
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