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Enantioselective Total Syntheses of (−)‐Rhazinilam, (−)‐Leucomidine B, and (+)‐Leuconodine F
Author(s) -
Dagoneau Dylan,
Xu Zhengren,
Wang Qian,
Zhu Jieping
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508906
Subject(s) - imine , chemistry , enantioselective synthesis , diastereomer , steric effects , catalysis , total synthesis , palladium , stereochemistry , homogeneous , combinatorial chemistry , medicinal chemistry , organic chemistry , physics , thermodynamics
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.