Silyl Triflate-Mediated Ring-Closure and Rearrangement in the Synthesis of Potential Bisfuran-Containing Intermediates of Aflatoxin Biosynthesis was written by Graybill, Todd L.;Casillas, Eduard G.;Pal, Kollol;Townsend, Craig A.. And the article was included in Journal of the American Chemical Society in 1999.Related Products of 14204-27-4 This article mentions the following:
The biosynthetic pathway to the potent mycotoxin aflatoxin B1 (I) is unusually long and complex, proceeding from anthraquinone to xanthone to coumarin nuclear types bearing fused tetrahydro- and bisdihydrofuran rings. A synthetic strategy is described involving two silyl triflate-mediated cyclization and rearrangement processes that have enabled both furofuran oxidation states to be readily achieved and undesired but thermodynamically favorable side reactions to be avoided in the preparation of these ring systems. In the first an o-methoxymethylphenylacetaldehyde is cyclized directly to the five-membered, differentially protected hemiacetal, while in the second this group, appropriately substituted, can be rearranged to a 4-trialkylsilyloxy-2,5-methano-1,3-benzodioxepane. The latter masked dialdehyde is sufficiently stable to strong base, mild acid, and oxidants to allow all needed aryl ring systems to be constructed. Using these methods, total syntheses of (闂?-versicolorin B (II), (闂?-versicolorin A (III), its hemiacetal, and its 6-deoxy derivative, (闂?-6-deoxyversicolorin A, have been achieved, and these are reported herein, as well as preparation of the Me ester of the putative o-carboxybenzophenone biosynthetic intermediate IV. In work described elsewhere, incorporation experiments with 13C-labeled forms of these compounds have made possible the complete elucidation of bisfuran biosynthesis characteristic of the first major phase of aflatoxin formation in vivo. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Related Products of 14204-27-4).
2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 14204-27-4
Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles