Synthesis of Enantiomerically Pure (−)-(S)-Brevicolline

Synthesis of Enantiomerically Pure (−)-(S)-Brevicolline

(−)-(S)-Brevicolline (1) and related β-carbolines were synthesized using an enantiomerically pure Michael-acceptor synthon (3). Subsequent Pictet−Spengler reaction afforded the tetrahydro-β-carboline skeleton, which, in turn, was transformed to the β-carboline by catalytic dehydrogenation.

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 1999-04, Vol.62 (4), p.577-579
Hauptverfasser: Mahboobi, Siavosh, Wiegrebe, Wolfgang, Popp, Alfred
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
catalytic activity
chemical reactions
chemical structure
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
synthesis
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Beschreibung
Zusammenfassung:(−)-(S)-Brevicolline (1) and related β-carbolines were synthesized using an enantiomerically pure Michael-acceptor synthon (3). Subsequent Pictet−Spengler reaction afforded the tetrahydro-β-carboline skeleton, which, in turn, was transformed to the β-carboline by catalytic dehydrogenation.
ISSN:0163-3864
1520-6025
DOI:10.1021/np980492h