Enantioselective Total Syntheses of (−)-Rhazinilam, (−)-Leucomidine B, and (+)-Leuconodine F

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 (-)-leucomidine B and (+)-leuconodine F. A substrate directed 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.


Published in:
Angewandte Chemie International Edition, 55, 2, 760-763
Year:
2016
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
1433-7851
Keywords:
Laboratories:




 Record created 2016-01-05, last modified 2018-01-28


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