Literature DB >> 19320481

Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system.

Shuhei Ikeda1, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi.   

Abstract

An enantiocontrolled entry to the tricyclic core of daphnicyclidin A with five chiral centers including an all-carbon quaternary center is reported. The synthesis features a highly diastereoselective conjugate addition of nitromethane, an Ireland-Claisen rearrangement, and a tandem acyliminium/Mannich-type reaction.

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Year:  2009        PMID: 19320481     DOI: 10.1021/ol9003405

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Total synthesis of the Daphniphyllum alkaloid daphenylline.

Authors:  Zhaoyong Lu; Yong Li; Jun Deng; Ang Li
Journal:  Nat Chem       Date:  2013-06-30       Impact factor: 24.427

2.  Asymmetric construction of rings A-D of daphnicyclidin-type alkaloids.

Authors:  Travis B Dunn; J Michael Ellis; Christiane C Kofink; James R Manning; Larry E Overman
Journal:  Org Lett       Date:  2009-12-17       Impact factor: 6.005

3.  An integrated screening system for the selection of exemplary substrates for natural and engineered cytochrome P450s.

Authors:  Naoki Kanoh; Ayano Kawamata-Asano; Kana Suzuki; Yusuke Takahashi; Takeshi Miyazawa; Takemichi Nakamura; Takashi Moriya; Hiroyuki Hirano; Hiroyuki Osada; Yoshiharu Iwabuchi; Shunji Takahashi
Journal:  Sci Rep       Date:  2019-12-02       Impact factor: 4.379

  3 in total

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