TY - JOUR
T1 - Bioinspired Indole Prenylation Reactions in Water
AU - Tanaka, Satomi
AU - Shiomi, Shinya
AU - Ishikawa, Hayato
N1 - Funding Information:
We gratefully acknowledge financial support through a JSPS KAKENHI Grant Numbers JP25288050, JP25670005, JP17H03059. We would also like to thank Prof. Hiroyuki Morita (University of Toyama) for the support and guidance.
Publisher Copyright:
© 2017 The American Chemical Society and American Society of Pharmacognosy.
PY - 2017/8/25
Y1 - 2017/8/25
N2 - 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.
AB - 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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U2 - 10.1021/acs.jnatprod.7b00464
DO - 10.1021/acs.jnatprod.7b00464
M3 - Article
C2 - 28803474
AN - SCOPUS:85028306484
VL - 80
SP - 2371
EP - 2378
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 8
ER -