Abstract
A concise, unified total synthesis of the two prenylated aromatic polyketides amorfrutins A and C, which exhibit various medicinally important biological profiles such as antimicrobial, PPARã modulating and quorum sensing inhibitory activities, has been achieved from commercially available 3,5-dimethoxybenzaldehyde in 38% and 10% overall yields through nine and ten steps, respectively. The key transformation for the synthesis of amorfrutin A was the Claisen rearrangement of a mono-O-(1,1-dimethylallyl)resorcinol derivative to install the C3- prenyl substituent, while that for the synthesis of amorfrutin C was the double Claisen rearrangement of a di-O-(1,1-dimethylallyl)resorcinol derivative to introduce the two prenyl groups at the C3 and C5 positions all at once.
Original language | English |
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Pages (from-to) | 1635-1641 |
Number of pages | 7 |
Journal | Bioscience, Biotechnology and Biochemistry |
Volume | 83 |
Issue number | 9 |
DOIs | |
Publication status | Published - 2019 |
Keywords
- Amorfrutin
- Amorpha fruticosa
- Claisen rearrangement
- Glycyrrhiza acanthocarpa
- Total synthesis
ASJC Scopus subject areas
- Biotechnology
- Analytical Chemistry
- Biochemistry
- Applied Microbiology and Biotechnology
- Molecular Biology
- Organic Chemistry