Literature DB >> 11843576

Short total synthesis of (+)-madindolines A and B.

Tomoyasu Hirose1, Toshiaki Sunazuka, Tatsuya Shirahata, Daisuke Yamamoto, Yoshihiro Harigaya, Isao Kuwajima, Satoshi Omura.   

Abstract

[reaction: see text] A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.

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Year:  2002        PMID: 11843576     DOI: 10.1021/ol017058i

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


  4 in total

1.  Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.

Authors:  Jie Guang; Qunsheng Guo; John Cong-Gui Zhao
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

2.  Synthesis of (+)-madindoline A and (+)-madindoline B.

Authors:  Lifeng Wan; Marcus A Tius
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005

3.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

4.  Auto-Tandem Catalysis: PdII -Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones.

Authors:  Claire J C Lamb; Bryan G Nderitu; Gemma McMurdo; John M Tobin; Filipe Vilela; Ai-Lan Lee
Journal:  Chemistry       Date:  2017-11-30       Impact factor: 5.236

  4 in total

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