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

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

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research