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Synthesis 2008(14): 2278-2282
DOI: 10.1055/s-2008-1067142
DOI: 10.1055/s-2008-1067142
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkAsymmetric Synthesis of Jaspine B (Pachastrissamine) via an Organocatalytic Aldol Reaction as Key Step
Weitere Informationen
Received
26 March 2008
Publikationsdatum:
18. Juni 2008 (online)
Publikationsverlauf
Publikationsdatum:
18. Juni 2008 (online)
Abstract
The asymmetric synthesis of jaspine B (pachastrissamine) using a (R)-proline-catalyzed enantioselective aldol reaction as key step is described. Jaspine B was synthesized from the commercially available and inexpensive 1-pentadecanal and the dihydroxyacetone equivalent 2,2-dimethyl-1,3-dioxan-5-one in nine steps, good overall yield (23.6%) and excellent stereoselectivity (de >98%, ee = 95%).
Key words
pachastrissamine (jaspine B) - asymmetric synthesis - aldol reaction - organocatalysis - proline
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