Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 2, Pages 760-763Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508906
Keywords
asymmetric synthesis; divergent synthesis; domino cyclization; heteroannulation; indole alkaloids
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Funding
- EPFL (Switzerland)
- Swiss State Secretariat for Education and Research (SER)
- Swiss National Science Foundation (SNSF)
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A divergent total synthesis of three structurally distinct natural products from imine 9 was accomplished through an approach featuring: 1) a Pd-catalyzed decarboxylative cross-coupling, and 2) heteroannulation of 9 with bromoacetaldehyde and oxalyl chloride to give tetrahydroindolizine 6 and dioxopyrrole 7, respectively. The former was converted into (-)-rhazinilam, while the latter was converted into (-)-leucomidineB and (+)-leuconodine F. A substratedirected highly diastereoselective reduction of a sterically unbiased double bond by using a homogeneous palladium catalyst was developed. A self-induced diastereomeric anisochronism (SIDA) phenomenon was observed for leucomidine B.
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