Abstract
Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.
Original language | English |
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Article number | 151891 |
Journal | Tetrahedron Letters |
Volume | 61 |
Issue number | 21 |
DOIs | |
Publication status | Published - 2020 May 21 |
Keywords
- DWAQMWPHCVWJMI-SMTRDTIPSA-N
- Natural product
- Terfestatin
- Total synthesis
- UTRHHGVQLUCOIT-NZXWXYQFSA-N
- p-Terphenyl
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry