Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02278
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [21J13995, 21K07055, 22H05366]
- AMED [JP21am0101084, JP22ama121054]
- Tokyo Biochemical Research Foundation
- Takeda Science Foundation
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The first total synthesis of marine sesterterpenoid ansellone G and phorbadione was achieved, and their HIV latency-reversing activity was evaluated.
The first total synthesis of marine sesterterpenoid ansellone G (2) was accomplished. This strategy utilizes the Prins cyclization reaction of a chloro-substituted homoallyl alcohol to synthesize the hydrobenzopyran skeleton. The preintroduction of the chloro groups facilitated the functional group transformation for 2 after constructing the carbon framework. Furthermore, we also successfully synthesized phorbadione (3) by dehydrating the tertiary alcohol. The HIV latency-reversing activity of the synthesized 2, 3, and deacetylated 2 was also evaluated.
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