Journal
ORGANIC LETTERS
Volume 23, Issue 5, Pages 1720-1725Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00151
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [T17K082100]
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from the AMED [JP19am0101084, JP20am0101084]
- Tokyo Biochemical Research Foundation
- Takeda Science Foundation
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The total synthesis and biological evaluation of the marine sesterterpenoid ansellone A, along with its analogues, were successfully carried out. The key to the success of the synthetic route was the Prins cyclization reaction enabled by the strategic use of the TfO group to stabilize the acid-labile tertiary allylic alcohol. The structure-activity relationship study indicated that the alcohol analogue exhibited more potent activity than compound 1.
The total synthesis and biological evaluation of the marine sesterterpenoid ansellone A (1), an HIV latency-reversing agent, and its analogues are reported. The key to the success of this synthetic route is a Prins cyclization reaction enabled by the strategic use of the TfO group for stabilization of the acid-labile tertiary allylic alcohol. The SAR study found the alcohol analogue to exhibit more potent activity than 1.
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