Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition

Abstract

An asymmetric tandem Friedel–Crafts alkylation/intermolecular macrolactonization of ortho-quinone methides with C3-substituted indoles was achieved by using a chiral N,N′-dioxide-scandium(iii) complex.

Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives

“…These results demonstrated that ferric ions (Fe 3+ ) could be selectively recognized by δ-carboline derivative 4a. 12 …”

Electrophilic amidomethylation of arenes with DMSO/MeCN reagents

“…The electrophilic aromatic C–H bond functionalization provides one of the most direct approaches to aryl derivatives, and plays an irreplaceable role in organic synthesis. 1 Generally, the electrophilic reagents are essential to the efficiency and selectivity of these reactions, affording one new C–C (Friedel–Crafts reaction) 2 or C–X (halogenation, 3 nitrogenation, 4 sulfonation 5 ) bond within one step in these electrophilic reactions. From the aspect of synthesis-efficiency and step-economy, 6 the development of electrophilic reactions to deliver complex molecules 7 along with multi-chemical bond construction under practical and mild reaction conditions is still highly desirable, and has been the pursuing goal of chemists.…”

Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

“…Among the different classes of macrocycles, macrolactones are especially unique compounds that exhibit biological activities and often function as enzyme inhibitors; they also showed applications in molecular recognition for supramolecular chemistry. For example, macrolactones synthesized from cholesterol derivatives have shown utility for molecular recognitions [ 8 ], and a synthetic macrodilactone exhibited enantioselective recognition of amino alcohols, as well as metal ions [ 9 ]. Naturally existing carbohydrate-based macrolactones or macrolides often exhibit many desirable biological activities for drug development [ 10 , 11 , 12 ].…”