Journal
ORGANIC LETTERS
Volume 12, Issue 23, Pages 5366-5369Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol101922h
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Funding
- National Science Foundation of China [20802043]
- Foundations of Education Commision of Shanghai Municipality [J50102]
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An expedient diastereoselective synthesis of highly functionalized indolo[2,3-alpha]quinolizidines adopting a cis H2/H12b geometry has been realized by a Pictet-Spengler/lactamization cascade sequence. The absolute stereochemistry at C2, C3, and C12b was governed by the originally created chirality of the Michael adduct through organocatalyzed conjugate addition of dialkyl malonates to alpha,beta-unsaturated aldehydes.
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