Efficient construction of the hexacyclic ring core of palau'amine: the pK_aconcept for proceeding with unfavorable equilibrium reactions

Abstract

Palau’amine has received a great deal of attention as an attractive synthetic target due to its intriguing molecular architecture and significant immunosuppressive activity, and we achieved its total synthesis in...

Utilizing the pKa Concept to Address Unfavorable Equilibrium Reactions in the Total Synthesis of Palau’amine

“…The first total synthesis of palau'amine was achieved by Baran's group in 2010 [14], and an asymmetric version was developed in 2011 [15]. In 2015 we successfully achieved the total synthesis [16], and in 2021 we developed an efficient method for constructing the hexacyclic ring system of palau'amine as part of our second-generation synthesis [17]. Not surprisingly, we encountered several difficulties during these synthetic studies.…”

One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3-Triazoles and 2-Hydroxymethylallyl Carbonates

“…Reported bioactivities of compounds containing 2-acylpryrrole include nonsteroidal anti-inflammatory, antipyretic, analgesic, cytotoxicity against human colon cancer cells, and antibacterial against methicillin-resistant Staphylococcus aureus . The 2-acylpyrroles are also versatile synthetic intermediates for alkaloids and heterocycles . Consequently, efficient and regioselective construction of pyrroles bearing an acyl group at 2-position has received significant attention, and a number of approaches have been developed to augment traditional methods such as Paal–Knorr synthesis and Barton–Zard reaction (Scheme A, a) .…”