Enantioselective Total Syntheses of (−)‐Rhazinilam, (−)‐Leucomidine B, and (+)‐Leuconodine F | Zendy

Dagoneau Dylan | Zendy; Xu Zhengren | Zendy; Wang Qian | Zendy; Zhu Jieping | Zendy

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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 international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201508906

Subject(s) - imine , enantioselective synthesis , chemistry , diastereomer , steric effects , catalysis , total synthesis , stereochemistry , palladium , combinatorial chemistry , organic chemistry

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.

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