82501-56-2

Usage

InChI:InChI=1/C6H5NO3/c7-4-3-6(9)10-5(4)1-2-8/h1-3H,7H2/b5-1+

Upstream product

• 158142-88-2 2,3-dichloro-4-(3,3-dimethyl-2-oxo-4-pentenyl)-4-hydroxy-2-cyclobutenone 
• 158142-89-3 3-amino-2-chloro-4-(3,3-dimethyl-2-oxo-4-pentenyl)-4-hydroxy-2-cyclobutenone 
• 158142-90-6 (E)-4-amino-5-(3,3-dimethyl-2-oxo-4-pentenylidene)-2(5H)-furanone 
• 158142-91-7 (E)-4-amino-5-(2-hydroxy-3,3-dimethyl-4-pentenylidene)-2(5H)-furanone 

Relevant academic research and scientific papers

Total Synthesis of the Antitumor Antibiotic Basidalin

The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.

Decarboxylative Knoevenagel-type reactions on tetronamides: Synthesis of 5-ylidene-4-amino-2(5 H)-furanones

A detailed account regarding the synthesis of 5-ylidene-2(5H)-furanones is given. The key step is a decarboxylative Knoevenagel-type reaction of tetronamides with various α-functionalized aldehydes. The synthesis of protected basidalin is presented. Georg

Ring transformation of 4-acylmethyl-2-chloro-4-hydroxy-2-cyclobutenone to γ-acylmethylenetetronate by thermal rearrangement: New synthetic aspect of squaric acid as a C4-synthon

Title cyclobutenones prepared from the TiCl4-catalyzed addition of a silyl enol ether to squaric acid dichloride and ester chloride were subjected to thermolysis (reflux in an aromatic solvent), and γ-acylmethylenetetronates were obtained stere