Total synthesis of angucyclines, 7 . Hydroaromatic angucyclines of the SF‐2315 type | Zendy

Krohn Karsten | Zendy; Khanbabaee Karamali | Zendy; Jones Peter G. | Zendy

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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 .

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