Mycothiazole, a polyketide heterocycle from a marine sponge

Glycothiohexide .ALPHA., a novel antibiotic produced by "Sebekia" sp., LL-14E605. III. Structural elucidation.

“…2. This fragment replaces the 2,3-dehydro-2-aminobutyric acid residue in nosiheptide (3). None of the proton resonances in this structural fragment showed coupling in the normal COSYexperiment performed on glycothiohexide a (1) or its methyl ether (2).…”

Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate

“…Two routes could be considered to lead to the aldehyde: Route a based on a [1,5] sigmatropic rearrangement promoted by the heating of the reaction mixture or route b catalyzed again by Ru, which is known to allow olefin isomerization to the α,β-unsaturated aldehyde. [28] Whatever the mechanism, the epoxide rearrangement proceeded faster than CM.…”

“…To the best of our knowledge, no synthesis of compound 2 has been reported so far and considering the potential interest in (-)-mycothiazole (1) itself, access to its derivatives presents a valuable challenge for organic chemists. The main difference between 1 and 2 is the presence of a conjugated homoallylic Z dienol in mycothiazole (1) and an allylic 1,1-dialkyl-1,2-ethanediol group in 2 ( Figure 1). …”

Reactivity of 2-substituted hydrazinecarbothioamides towards tetracyanoethylene and convenient synthesis of (5-amino-2-diazenylthiazolylmethylene)malononitrile derivatives

“…[1][2][3][4][5] For example, naturally occurring and synthetic thiazoles find applications as antibiotics and anti-inflammatories, [4][5][6][7][8] while selected aminothiazoles act as inhibitors of human cancer and Alzheimer`s disease. [9][10][11] The syntheses of thiazoles and 2-aminothiazoles have been studied extensively, 12,13 however, the preparation of 5-aminothiazoles has not been so widely reported.…”