Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.
Department of Environmental and Molecular Health Sciences, Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto 862-0973, Japan.
Org Lett. 2021 Mar 5;23(5):1720-1725. doi: 10.1021/acs.orglett.1c00151. Epub 2021 Feb 11.
The total synthesis and biological evaluation of the marine sesterterpenoid ansellone A (), 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 .
本文报道了海洋甾体 Ansellone A()的全合成及生物评价，Ansellone A 是一种 HIV 潜伏逆转剂及其类似物。该合成路线的关键在于巧妙地利用 TfO 基团稳定酸不稳定的叔烯丙醇，实现了 Prins 环化反应。SAR 研究发现，醇类似物的活性强于 Ansellone A。
