Total Synthesis and Biological Evaluation of the Potent HIV Latency-Reversing Agent Ansellone A and its Analogues.

Affiliation

Yanagihara M(1), Murai K(1), Kishimoto N(2), Abe T(2), Misumi S(2), Arisawa M(1).
Author information:
(1)Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.
(2)Department of Environmental and Molecular Health Sciences, Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto 862-0973, Japan.

Abstract

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.