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Total synthesis of angucyclines, 7 . Hydroaromatic angucyclines of the SF‐2315 type
Author(s) -
Krohn Karsten,
Khanbabaee Karamali,
Jones Peter G.
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199511277
Subject(s) - chemistry , diol , adduct , silanol , phenol , intramolecular force , organic chemistry , ether , photooxygenation , sulfuric acid , yield (engineering) , medicinal chemistry , catalysis , oxygen , materials science , singlet oxygen , metallurgy
Osmylation of the Diels‐Alder adduct 3 afforded the cis ‐diol 4 , which was dehydrated by acid treatment to the phenol 6. Reaction with tetrafluoroboric acid converted the diol 4 by intramolecular acyl shift into the acetate 7. The relative stereochemistry of 7 was determined by single‐crystal X‐ray analysis. Photooxygenation of 4 afforded the C‐1 carbonyl compound 8 and treatment with sulfuric acid the silanol 9. Functionalization of C‐6 was achieved by treatment of 4 with methanolic KOH to yield the cis ‐methyl ether 11 .