Literature DB >> 18950180

Structure and absolute stereochemistry of the anticancer agent EBC-23 from the Australian rainforest.

Lin Dong1, Victoria A Gordon, Rebecca L Grange, Jenny Johns, Peter G Parsons, Achim Porzelle, Paul Reddell, Heiko Schill, Craig M Williams.   

Abstract

EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.

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Year:  2008        PMID: 18950180     DOI: 10.1021/ja807133p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  Rapid total syntheses utilizing "supersilyl" chemistry.

Authors:  Brian J Albert; Yousuke Yamaoka; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-08       Impact factor: 15.336

2.  Total Synthesis of (-)-Nahuoic Acid Ci (Bii).

Authors:  Qi Liu; Yifan Deng; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-09-21       Impact factor: 15.419

3.  Total Synthesis of (±)-Vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Huw M L Davies; Craig M Williams
Journal:  Aust J Chem       Date:  2009       Impact factor: 1.321

4.  Stereoselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols.

Authors:  Fangzheng Li; William R Roush
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

5.  Enantioselective Total Synthesis of (+)-EBC-23, a Potent Anticancer Agent from the Australian Rainforest.

Authors:  Arun K Ghosh; Che-Sheng Hsu
Journal:  J Org Chem       Date:  2021-04-19       Impact factor: 4.354

  5 in total

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