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Synfacts 2005(0): 0011-0011
DOI: 10.1055/s-2005-865351
DOI: 10.1055/s-2005-865351
Synthesis of Natural Products and Drugs
Georg Thieme Verlag Stuttgart · New York
Total Syntheses of Benzastatin E and Virantmycin
Rezensent(en): Philip KocienskiM. Ori, N. TODA, K. Takami, K. Tago, H. Kogen*
Sankyo Co., Tokyo, Japan
Stereospecific Synthesis of 2,2,3-Trisubstituted Tetrahydroquinolines: Application to the Total Syntheses of Benzastatin E and Natural Virantmycin
Tetrahedron 2005, 61: 2075-2104
Sankyo Co., Tokyo, Japan
Stereospecific Synthesis of 2,2,3-Trisubstituted Tetrahydroquinolines: Application to the Total Syntheses of Benzastatin E and Natural Virantmycin
Tetrahedron 2005, 61: 2075-2104
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. Juli 2005 (online)
Key words
rearrangement - aziridinium ion -
Significance
The first synthesis of the natural (-)-antipode of Virantmycin is reported. Virantmycin is a potent inhibitor of RNA and DNA viruses. It is isolated from Streptomyces nitrosporeus. The related benzstatins inhibit glutamate toxicity and lipid peroxidation.
Comment
The difficult stereoselective construction of a chiral quaternary center was accomplished by a stereospecific rearrangement of an α,α-disubstituted indoline-2-methanol B via aziridinium ion C.