ABSTRACT
An efficient sequential double-annulation strategy has been developed to afford a series of unsymmetrical acridines with high yield and regioselectivity for the first time. This simple protocol enables the sequential assembly of two aromatic rings from simple starting materials. The reaction proceeds via modified Friedländer annulation and subsequent base-mediated benzannulation with acrylates as Michael acceptors. A range of substrate scope and functional group tolerance is observed. Late-stage synthetic modification is also explored to access novel unsymmetrical acridines in good yield.
ABSTRACT
The inthomycin family of antibiotics, isolated from Streptomyces strains, are interesting molecules for synthesis due to their characteristic common oxazole polyene chiral allylic ß-hydroxycarbonyl fragments and significant biological activities. The full structural motif of the inthomycins is found in several more complex natural products including the oxazolomycins, 16-methyloxazolomycin, curromycins A and B, and KSM-2690. This review summarises the application of various efforts towards the synthesis of inthomycins and their analogues systematically.
ABSTRACT
A cationic oxazaborolidinium-catalyzed asymmetric Mukaiyama aldol reaction of (1-methoxy-2-methyl-propenyloxy)-trimethylsilane with various aldehydes including α,ß-disubstituted acroleins has been developed in high yields and enantioselectivities. The synthetic utility of this methodology was demonstrated in the first short synthesis of naturally occurring inthomycin C in high enantiopurity.
Subject(s)
Biological Products/chemical synthesis , Oxazoles/chemical synthesis , Aldehydes/chemistry , Biological Products/chemistry , Boron Compounds/chemistry , Catalysis , Combinatorial Chemistry Techniques , Molecular Structure , Oxazoles/chemistry , Silanes/chemistry , StereoisomerismABSTRACT
A catalytic route toward chiral Morita-Baylis-Hillman esters by asymmetric coupling between alpha,beta-acetylenic esters, aldehydes, and trimethylsilyl iodide has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities, and the products can be transformed into beta-branched derivatives in a single step and with excellent retention of configuration. TMS = trimethylsilyl.
