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1. Pd(II)-Catalyzed Aminofluorination of Alkenes in Total Synthesis 6-(R)-Fluoroswainsonine and 5-(R)-Fluorofebrifugine.

Author

Wu L, Chen P, and Liu G

Subjects
Alkaloids chemistry, Catalysis, Molecular Structure, Piperidines chemistry, Pyridines chemistry, Quinazolines chemistry, Stereoisomerism, Swainsonine chemical synthesis, Swainsonine chemistry, Alkaloids chemical synthesis, Alkenes chemistry, Palladium chemistry, Piperidines chemical synthesis, Quinazolines chemical synthesis, Swainsonine analogs & derivatives
Abstract

The total syntheses of two fluorinated alkaloids, 6-(R)-fluoroswainsonine and 5-(R)-fluorofebrifugine, are described. Both encompass (4aS,7R,8aR)-7-fluoro-5-tosylhexahydro-4H-[1,3]dioxino[5,4-b]pyridine as a key synthon which is obtained through a further optimized palladium-catalyzed aminofluorination of alkenes with high diastereoselectivity. 6-(R)-Fluoroswainsonine is synthesized from the key synthon in 14 steps, and 5-(R)-fluorofebrifugine requires a sequential 15-step transformation.

Published
2016
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