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DOI: 10.1055/s-0033-1340354
Synthesis of Jerantinine E
Publikationsverlauf
Publikationsdatum:
13. Dezember 2013 (online)
Significance
Jerantinine E was isolated in 2008 from Tabernaemontana corymbosa. This Aspidosperma alkaloid shows potent cytotoxic activity against human KB cells. The authors report the first synthesis of racemic jerantinine E. Separation of (+)- and (–)-jerantinine E allowed for further biological evaluation. Additionally, investigations into the mode of action revealed potent inhibition of tubulin polymerization.
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Comment
The synthesis commenced with an organo-lithium addition to Weinreb amide B. Treatment of the resulting ketone D with copper (II) triflate resulted in a formal homo-Nazarov cyclization, which gave tetracyclic intermediate E as a single diastereomer. A double-alkylation sequence of F followed by selective demethylation of G afforded jerantinine E in 17 steps from A and 16% overall yield.
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