Literature DB >> 16119934

Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radical rearrangement.

Masahiro Toyota1, Takeshi Asano, Masataka Ihara.   

Abstract

Total syntheses of serofendic acids A (1a) and B (1b) are described. The key strategic element of the approach involves the novel tin-free homoallyl-homoallyl radical rearrangement of 5 for the construction of bicyclo[2.2.2]octane ring system 4. In addition, the conversion of methyl atisirenoate 2 to serofendic acids A (1a) and B (1b) was achieved on the basis of the Michael reaction of sodium thiomethoxide.[reaction: see text]

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Year:  2005        PMID: 16119934     DOI: 10.1021/ol051411t

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


  5 in total

Review 1.  Recent advances in the chemistry and biology of naturally occurring antibiotics.

Authors:  K C Nicolaou; Jason S Chen; David J Edmonds; Anthony A Estrada
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Stereoselective semi-synthesis of the neuroprotective natural product, serofendic acid.

Authors:  Dimitri Perusse; Michael J Smanski
Journal:  Medchemcomm       Date:  2019-04-23       Impact factor: 3.597

3.  Total syntheses of (+/-)-platencin and (-)-platencin.

Authors:  K C Nicolaou; G Scott Tria; David J Edmonds; Moumita Kar
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

4.  A unified approach to ent-atisane diterpenes and related alkaloids: synthesis of (-)-methyl atisenoate, (-)-isoatisine, and the hetidine skeleton.

Authors:  Emily C Cherney; Justin M Lopchuk; Jason C Green; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-08-29       Impact factor: 15.419

5.  Metabolites of ginger component [6]-shogaol remain bioactive in cancer cells and have low toxicity in normal cells: chemical synthesis and biological evaluation.

Authors:  Yingdong Zhu; Renaud F Warin; Dominique N Soroka; Huadong Chen; Shengmin Sang
Journal:  PLoS One       Date:  2013-01-30       Impact factor: 3.240

  5 in total

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