The indenobenzazepine-spirobenzylisoquinoline rearrangement; stereocontrolled syntheses of (±)-raddeanine and (±)-yenhusomine
✍ Scribed by Gábor Blaskó; Natesan Murugesan; Alan J. Freyer; Daniella J. Gula; Bilge Şener; Maurice Shamma
- Book ID
- 104234179
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 276 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Stereoselective rearrangement of indenobenzazepine cis ketoZs 2 and 5 with TFAA in pyridine _ _ produces spirobenzyZisoquinoZines 2 and 6.. respectively. The latter product is also obtained by rearrangement of trans ketoi! 7.
-The transformation of ketoZs J. and 7_must, therefore, proceed through the intermediacy of aziridiniwn cation 2. A similar process obtains in the transfomation of 2 to z. NaBH4 reduction of 3 gives 1+1-raddeanine (4). _ Rearrangement of dio7, 10 supplies -2 directly. (+I-Yenhusomine ( 13) is obtained from the rearrangement of either dioL 11 or 12. In --Zike fashion, dioZs 14 and 15 supply spirobenzylisoquinoZine 17.