685135-81-3

Basic information

• Product Name: Rugulotrosin A
• Synonyms: Rugulotrosin A
• CAS NO: 685135-81-3
• Molecular Formula: C32H30O14
• Molecular Weight: 638.5722
• Mol File: 685135-81-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Rugulotrosin A(CAS DataBase Reference)
• NIST Chemistry Reference: Rugulotrosin A(685135-81-3)
• EPA Substance Registry System: Rugulotrosin A(685135-81-3)

Safety Data

• Hazardous Substances Data: 685135-81-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Rugulotrosin A is used as an antibacterial agent for its ability to effectively combat a broad spectrum of Gram-positive bacteria. Its potent activity makes it a promising candidate for the development of new antibiotics to address the growing concern of antibiotic resistance.
Used in Research and Development:
In the field of microbiology and pharmaceutical research, Rugulotrosin A serves as a valuable compound for studying the mechanisms of action against Gram-positive bacteria. This can lead to a better understanding of bacterial resistance and the development of more effective treatments.

Upstream product

• 1265471-63-3 methyl 5-hydroxy-7-methyl-4-oxo-4H-chromene-2-carboxylate 
• 119478-74-9 (S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enone 
• 1616780-08-5 methyl (4S,4aS)-4-(tert-Butyldimethylsilyloxy)-1-hydroxy-8-methoxy-6-methyl-9-oxo-2,3,4,4a-tetrahydroxanthene-4a-carboxylate 

Relevant articles and documents

Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer

Chiral, dimeric natural products containing complex structures and interesting biological properties have inspired chemists and biologists for decades. A seven-step total synthesis of the axially chiral, dimeric tetrahydroxanthone natural product rugulotrosin A is described. The synthesis employs a one-pot Suzuki coupling/dimerization to generate the requisite 2,2′-biaryl linkage. Highly selective point-to-axial chirality transfer was achieved using palladium catalysis with achiral phosphine ligands. Single X-ray crystal diffraction data were obtained to confirm both the atropisomeric configuration and absolute stereochemistry of rugulotrosin A. Computational studies are described to rationalize the atropselectivity observed in the key dimerization step. Comparison of the crude fungal extract with synthetic rugulotrosin A and its atropisomer verified that nature generates a single atropisomer of the natural product.

Synthesis method of dimeric molecule in natural product tetrahydroxanthone

The invention discloses a synthesis method of a dimeric molecule in a natural product tetrahydroxanthone. According to the method, a compound as shown in a formula 1 is used as a starting raw material; asymmetric total synthesis of the dimeric molecule in the tetrahydroxanthone is completed through michael addition, bromation and elimination, lindgren oxidation and methyl esterification, the bromation, negishi coupling, ethylene glycol protection and ozone cutting off, the 6pi electrocyclization in series with knoevenagel condensation, aromatization, methyl iodide protection, the removal of the ethylene glycol protection, epoxidation, epoxide ring-opening, dess-martin oxidation, samarium diiodide reduction, methyl removal, the removal of t-butyldimethylsilyl protecting group, iodination, a suzuki-miyaura coupling one-pot method and the methyl removal. A synthetic route is reasonable in design; the raw material is low-cost and is easily obtained; the loss brought by chiral separation is avoided through starting from a chiral raw material; an intermediate in a key reaction is easily modified; a series of analogues of the dimeric molecule in the tetrahydroxanthone can be synthesized by utilizing the method; a foundation is laid for the subsequent chemical research of a medicine.