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The Hydroxylated, Tetracyclic Bisquinolizidine Alkaloids Baptifoline and Epibaptifoline: Enantioselective Synthesis and Unambiguous Assignment of their Configuration at C‐13
Author(s) -
Goller Jessica,
Hübschle Christian B.,
Breuning Matthias
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801126
Subject(s) - chemistry , stereocenter , enantioselective synthesis , stereochemistry , absolute configuration , alkaloid , alcohol , organic chemistry , catalysis
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: 7 R , 9 R , 11 R , 13 R ) and in exo (β) position in epibaptifoline (configuration: 7 R , 9 R , 11 R , 13 S ).