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Efficient Syntheses of Diverse, Medicinally Relevant Targets Planned by Computer and Executed in the Laboratory
The Chematica program was used to autonomously design synthetic pathways to eight structurally diverse targets, including seven commercially valuable bioactive substances and one natural product, which offer significant yield improvements and cost savings over previous approaches, or provide alternatives to patented routes. Expand
Total synthesis of 7'-desmethylkealiiquinone.
The total synthesis of an analogue of the marine alkaloid kealiiquinone has been completed through application of an intramolecular Diels-Alder reaction of an imidazole-containing enyne via a reaction with glyoxal in the presence of KCN. Expand
Synthesis of 2-imidazolones and 2-iminoimidazoles.
Treatment of the salt with commercial bleach leads to effective oxidation at C2 and the formation of the corresponding imidazolone and an N-chloro amide affords the corresponding protected 2-amino derivative in good yield. Expand
Intramolecular Diels-Alder chemistry of 4-vinylimidazoles.
An investigation of 4-vinylimidazoles as diene components in the intramolecular Diels-Alder reaction is described, establishing that amino linkers were generally more effective than either ethers or esters. Expand
Total Synthesis of 7′-Desmethylkealiiquinone, 4′-Desmethoxykealiiquinone, and 2-Deoxykealiiquinone
Synthetic approaches to the imidazonaphthoquinone core of kealiiquinone and related Leucetta-derived alkaloids are described and endgame strategies were evaluated; however, these efforts did not lead to completion of a synthesis of kealiquin one but did provide access to other closely related analogues. Expand
Total syntheses of isonaamine C and isonaamidine E.
The total syntheses of two alkaloids isolated from a marine sponge of the Leucetta sp. have been accomplished in 6 and 7 steps starting from a 4,5-diiodoimidazole derivative. Grignard mediatedExpand
Total synthesis and cytotoxicity of Leucetta alkaloids.
The total synthesis of a number of representative natural products isolated from Leucetta and Clathrina sponges containing a polysubstituted 2-aminoimidazole are described, and for comparative purposes a series of naphthimodazole-containing family members are included. Expand
Urocanic acid derivatives have served as useful starting materials in several total synthesis endeavors in our lab. This paper describes a convenient, large-scale synthesis of several derivatives ofExpand
Intramolecular Diels—Alder Chemistry of 4‐Vinylimidazoles.
The intramolecular Diels—Alder cycloaddition of amide-, ester- or ether-tethered dienylimidazoles is studied concerning the influence of the nature of tether and N-protecting groups.