Literature DB >> 31416310

Asymmetric Total Syntheses of Rhynchophylline and Isorhynchophylline.

Zhihong Zhang, Wei Zhang, Fangyuan Kang, Fanny C F Ip, Nancy Y Ip, Rongbiao Tong.   

Abstract

The asymmetric total syntheses of (-)-rhynchophylline and (+)-isorhynchophylline were achieved in 17 and 16 steps, respectively, from butanal and ethyl acrylate. Our synthesis features Carreira ring expansion to construct the tetracyclic spirooxindole core in high diastereoselectivity and the use of Bosch's chiral lactam for preparation of enantioenriched cyclic imine.

Entities:  

Year:  2019        PMID: 31416310     DOI: 10.1021/acs.joc.9b01977

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  An approach to new chiral bicyclic imines and amines via Horner-Wadsworth-Emmons reaction.

Authors:  Jakub Iwanejko; Mateusz Sowiński; Elżbieta Wojaczyńska; Tomasz K Olszewski; Marcin Górecki
Journal:  RSC Adv       Date:  2020-04-09       Impact factor: 3.361

  1 in total

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