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Unusual biomimetic oxidations of indoles: synthesis of suaveoline and an alkaloid G analogue

✍ Scribed by Patrick D. Bailey; Keith M. Morgan; Georgina M. Rosair; Rhodri Ll. Thomas

Book ID
104262462
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
314 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.

πŸ“œ SIMILAR VOLUMES

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