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
• Article Data: 2

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

Different sources of media describe the Uses of 685135-81-3 differently. You can refer to the following data:
1. Rugulotrosin A is a symmetric dimer isolated from an uncharacterised species of Penicillium. Rugulotrosin A displays significant antibacterial activity against a wide range of Gram positive bacteria, but has received no further investigation.
2. Rugulotrosin A is a symmetric dimer which displays antibacterial activity.

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.