Total Synthesis and Biological Evaluation of the Potent HIV Latency-Reversing Agent Ansellone A and its Analogues
Mizushi Yanagihara, Kenichi Murai, Naoki Kishimoto, Towa Abe, Shogo Misumi, Mitsuhiro Arisawa
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.
Topics & Concepts
ReversingChemistryPrins reactionTotal synthesisAllylic alcoholAlcoholHuman immunodeficiency virus (HIV)Latency (audio)Combinatorial chemistryBiological activityStereochemistryAllylic rearrangementOrganic chemistryBiochemistryIn vitroVirologyCatalysisBiologyEngineeringMaterials scienceComposite materialElectrical engineeringSynthetic Organic Chemistry MethodsSynthesis and Catalytic ReactionsMarine Sponges and Natural Products