The Hydroxylated, Tetracyclic Bisquinolizidine Alkaloids Baptifoline and Epibaptifoline : Enantioselective Synthesis and Unambiguous Assignment of their Configuration at C-13

Titelangaben

Goller, Jessica ; Hübschle, Christian B. ; Breuning, Matthias:
The Hydroxylated, Tetracyclic Bisquinolizidine Alkaloids Baptifoline and Epibaptifoline : Enantioselective Synthesis and Unambiguous Assignment of their Configuration at C-13.
In: European Journal of Organic Chemistry. (2019) Heft 5 . - S. 895-899.
ISSN 1099-0690
DOI: https://doi.org/10.1002/ejoc.201801126

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Abstract

The epimeric bisquinolizidines baptifoline and epibaptifoline are C-13 hydroxylated derivatives of the well-known lupine alkaloid anagyrine. We synthesized both compounds from 11-allylcytisine and determined their uncertain configuration at the C-13 stereocenter by NMR, chemical transformation, and X-ray. The alcohol function was found to be in endo (α) position in baptifoline (configuration: 7R, 9R, 11R, 13R) and in exo (β) position in epibaptifoline (configuration: 7R, 9R, 11R, 13S).