Journal
SYNTHESIS-STUTTGART
Volume -, Issue 22, Pages 3675-3679Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260243
Keywords
Michael addition; organocatalysis; cyclization; enantioselectivity; reduction
Categories
Funding
- National Natural Science Foundation of China [20802043, 21072125]
- National Basic Research Program of China (973 Program) [2010CB833204]
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An organocatalyzed one-pot Michael addition and Pictet-Spengler sequence utilizing beta-keto amide and aliphatic alpha,beta-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.
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