np7b00464_si_001.pdf (42.78 MB)
Bioinspired Indole Prenylation Reactions in Water
journal contribution
posted on 2017-08-13, 00:00 authored by Satomi Tanaka, Shinya Shiomi, Hayato IshikawaIsoprene 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.