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Absolute configuration of the rubiginones and photo-induced oxidation of the C1 hydroxyl of the antibiotics to a ketone

✍ Scribed by Masahisa Oka; Masataka Konishi; Toshikazu Oki; Mamoru Ohashi


Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
143 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis


The absolute stereochemistry of rubiginones Al, A2, Bl, B , Cl and C2 has been established by NMR spectral analysis using the 0-methylmandelate met od. t A facile photoinduced oxidation of rubiginones Al, Bl and Cl to rubiginones A2, B2 and C2, respectively, is discussed in relation to the absolute stereochemistry.


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## A smzoselective Lewis acid-promoted cycknddition reaction of S-hydroxy-1,4+aphthoquinone and dienol(12) gave a key inttmmiiate (14) which was traqformed into the ti& compound (18) in 35% overall yield. The discovery of new mmbers of the angucycliaone group of antibiotics' in r#xnt years has sti