Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 43, Pages 13529-13532Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608138
Keywords
alkaloids; allylic alkylation; asymmetric catalysis; quaternary centers; total synthesis
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Funding
- NIH-NIGMS [R01GM080269]
- Amgen
- Gordon and Betty Moore Foundation
- Caltech
- NSF [DGE-1144469]
- Toray Industries Inc.
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The successful application of dihydropyrido[1,2-a]indolone (DHPI) substrates in Pd-catalyzed asymmetric allylic alkylation chemistry facilitates rapid access to multiple alkaloid frameworks in an enantioselective fashion. Strategic bromination at the indole C3 position greatly improved the allylic alkylation chemistry and enabled a highly efficient Negishi cross-coupling downstream. The first catalytic enantioselective total synthesis of (-)-goniomitine, along with divergent formal syntheses of (+)-aspidospermidine and (-)-quebrachamine, are reported herein.
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