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Total synthesis of angucyclines, 7. Hydroaromatic angucyclines of the SF-2315 type

✍ Scribed by Krohn, Karsten ;Khanbabaee, Karamali ;Jones, Peter G.

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 622 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1995199511277

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

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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