1300041-53-5

Basic information

• Product Name: (+)-fusarisetin A
• CAS NO: 1300041-53-5
• Molecular Weight: 389.492
• Mol File: 1300041-53-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+)-fusarisetin A(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-fusarisetin A(1300041-53-5)
• EPA Substance Registry System: (+)-fusarisetin A(1300041-53-5)

Safety Data

• Hazardous Substances Data: 1300041-53-5(Hazardous Substances Data)

Usage

Description

(+)-Fusarisetin A is a pentacyclic fungal metabolite first isolated from Fusarium species. It is an unusual pentacyclic metabolite related to equisetin and has been identified as an inhibitor of acini.
Used in Pharmaceutical Industry:
(+)-Fusarisetin A is used as an inhibitor of acinar morphogenesis for studying tumor cell motility and potentially developing treatments for cancer-related conditions. It has been identified from a natural product screen using a three-dimensional matrigel-induced bioassay to study acinar morphogenesis, making it the first inhibitor of acini reported in the literature.
Used in Research Applications:
(+)-Fusarisetin A is used as a research tool for investigating the mechanisms of acinar morphogenesis and cell migration, as it has been reported to inhibit acinar morphogenesis, cell migration, and invasion in a 3D-matrigel assay system designed for this purpose. This makes it a valuable compound for understanding the processes involved in tumor cell motility and the development of potential therapeutic agents.

Upstream product

• 57749-43-6 (-)-equisetin 
• 1447817-53-9 C₂₃H₄₀O₃Si 
• 1447817-52-8 C₂₂H₄₀O₂Si 
• 205494-87-7 C₁₁H₁₈O 
• 1447817-67-5 C₂₃H₃₅NO₆ 
• 1447817-66-4 C₃₅H₆₃NO₆Si₂ 
• 1447817-65-3 C₂₅H₄₂O₄Si 
• 1447817-63-1 C₂₆H₄₆O₇SSi 
• 1447817-62-0 C₂₆H₄₆O₆SSi 
• 1447817-61-9 C₂₅H₄₃F₃O₇S₂Si 
• 1447817-60-8 C₂₄H₄₄O₅SSi 
• 1447817-59-5 C₁₈H₃₀O₅S 
• 1447817-57-3 C₂₄H₄₂O₅SSi 
• 1447817-58-4 C₁₈H₂₈O₅S 

Relevant articles and documents

Biomimetic synthesis of equisetin and (+)-fusarisetin A

(+)-FusarisetinA belongs to a group of acyl tetramic acid natural products that show potential anticancer activity. Equisetin, a biogenetically related acyl tetramic acid, contains the basic skeleton of (+)-fusarisetinA. We proposed that equisetin and (+)-fusarisetinA share a biosynthetic pathway that starts with naturally occurring (S)-serine and an unsaturated fatty acid. In support of this hypothesis, we have demonstrated that a cyclization sequence involving an intramolecular Diels-Alder reaction followed by a Dieckmann cyclization of polyenoylamino acid yielded equisetin. The aerobic oxidation of equisetin, promoted by either MnIII/O2 or a reactive oxygen species (ROS) produced by visible-light chemistry, gave peroxyfusarisetin, which could be easily reduced to (+)-fusarisetinA. We report herein detailed information on the biogenetic synthesis of equisetin and (+)-fusarisetinA. Make the change to bio! Biomimetic synthesis of equisetin and (+)-fusarisetinA was achieved based on a biosynthetic hypothesis. An intramolecular Diels-Alder reaction followed by a Dieckmann cyclization of polyenoylamino ester furnished equisetin. The aerobic oxidation of equisetin to give (+)-fusarisetinA was mediated by a MnIII/O2 system or reactive oxygen species (ROS) (see scheme). Copyright

Total synthesis of (+)-fusarisetin A

Herein we report the full details of our efforts toward the application of Pauson-Khand reaction for the stereoselective construction of the trans-decalin subunit with a C16 quaternary stereocenter of fusarisetin A, which led to the asymmetric total synth

Total synthesis of (-)-fusarisetin A and reassignment of the absolute configuration of its natural counterpart

The first total synthesis of (-)-fusarisetin A, the enantiomer of naturally occurring acinar morphogenesis inhibitor (+)-fusarisetin A, was accomplished in 13 steps, leading to the reassignment of the absolute configuration of the natural product. The synthesis featured a Lewis acid-promoted intramolecular Diels-Alder reaction, a Pd-catalyzed O→C allylic rearrangement, a chemoselective Wacker oxidation, and a Dieckmann condensation/hemiketalization cascade.