28882-53-3Relevant academic research and scientific papers
Total synthesis of Angucyclines. Part 18: A short and efficient synthesis of (+)-ochromycinone
Krohn, Karsten,Sohrab, Md. Hossain,Floerke, Ulrich
, p. 713 - 718 (2004)
A short and highly enantiospecific (seven steps, 99% ee) synthesis of (+)-ochromycinone 2 in 19% overall yield is reported. Key steps are the regioselective Diels-Alder reaction of the juglone derivative 4 with the mixture of dienes 5 and 9 derived from 3-methylcyclohexanone (99% ee) and the photooxidation of 1-deoxyochromycinone 3 to the natural ketone 2. A pronounced concentration dependence of the specific rotation was observed for (+)-ochromycinone 2 in CHCl3.
Angucyclinone antibiotics: Total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755
Kaliappan, Krishna P.,Ravikumar, Velayutham
, p. 6116 - 6126 (2008/02/10)
(Chemical Equation Presented) A concise and highly enantioselective route has been developed for the synthesis of angucyclinone-type natural products. Utilizing this strategy, total syntheses of five natural products YM-181741, (+)-ochromycinone, (+)-rubi
Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: Enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2
Sato, Kenichiro,Asao, Naoki,Yamamoto, Yoshinori
, p. 8977 - 8981 (2007/10/03)
An efficient synthetic approach to angucyclinone antibiotics, (+)-ochromycinone and (+)-rubiginone B2, is reported. The key step involves the facile formation of 2,3-dihydrophenantren-4(1H)-one skeleton, an important framework of angucyclinone
Short and efficient enantioselective total synthesis of angucyclinone type antibiotics (+)-rubiginone B2 and (+)-ochromycinone
Carreno, M. Carmen,Urbano, Antonio,Di Vitta, Claudio
, p. 817 - 818 (2007/10/03)
The enantioselective total synthesis of antibiotics rubiginone B2 and ochromycinone is achieved from enantiopure (S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone and a racemic vinylcyclohexene through a short sequence involving a tandem Diels-Alder reaction-sulfoxide elimination process with simultaneous kinetic resolution of the racemic diene, followed by controlled aromatization and functional group deprotection.
Total syntheses of the angucyclinone antibiotics (+)-emycin A and (+)-ochromycinone
Larsen, David S.,O'Shea, Michael D.,Brooker, Sally
, p. 203 - 204 (2007/10/03)
The first asymmetric synthesis of the angucyclinone antibiotics, emycin A and ochromycinone, is achieved via a short, efficient sequence from 5-hydroxy-1,4-naphthoquinone with the key step being an effective kinetic resolution of a racemic diene in a Diel
