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Synthesis 2011(22): 3675-3679
DOI: 10.1055/s-0030-1260243
DOI: 10.1055/s-0030-1260243
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Cascade Sequence to Indoloquinolizidines and Its Application in the Synthesis of epi-Geissochizol
Further Information
Received
18 July 2011
Publication Date:
27 September 2011 (online)
Publication History
Publication Date:
27 September 2011 (online)
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Abstract
An organocatalyzed one-pot Michael addition and Pictet-Spengler sequence utilizing β-keto amide and aliphatic α,β-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-a]quinolizidines as a mixture of keto and enol tautomers. Such tautomeric pairs were transformed into stable compounds with an E-ethylidenyl group in telescoped steps. This method was successfully applied in the synthesis of epi-geissoschizol.
Key words
Michael addition - organocatalysis - cyclization - enantioselectivity - reduction
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