A flexible strategy for the synthesis of tri- and tetracyclic lupin alkaloids: Synthesis of (+)-cytisine, (±)-anagyrine, and (±)-thermopsine

Angewandte Chemie - International Edition

Volumn 45, Issue 15, 2006, Pages 2419-2423

  Gray, Diane ^a   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Alkaloids; Cyclization; Natural products; Nucleophilic addition; Synthetic methods

Indexed keywords

ALKALOIDS; CYCLIZATION; NATURAL PRODUCTS; NUCLEOPHILIC ADDITION; SYNTHETIC METHODS;

CHEMICAL BONDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

ALKALOID; ANAGYRINE; AZOCINE DERIVATIVE; CYTISINE; FUSED HETEROCYCLIC RINGS; QUINOLIZINE DERIVATIVE; THERMOSPINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; AZOCINES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE; QUINOLIZINES;

EID: 33746279633     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504015     Document Type: Article

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69. i = 3.0 ± 0.65 nM for (-)-cytisine. This low level of activity could also be attributed to a small (ca. 0.4 %) level of contamination by (-)-cytisine as a consequence of the kinetic resolution step involved. We thank Professor Susan Wonnacott and Neal Innocent (University of Bath) for this determination.