Literature DB >> 22085260

Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.

Hee Nam Lim1, Kathlyn A Parker.   

Abstract

The first total synthesis of (-)-arabilin, a Streptomyces metabolite that inhibits hormone activation of the androgen receptor, has been completed. The key step, a [1,7]-hydrogen shift, establishes the enol ether-containing skipped-tetraene substructure. This nonenzymatic pericyclic reaction is considered to be biomimetic.
© 2011 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 22085260      PMCID： PMC3320024          DOI： 10.1021/ja209459f

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


  14 in total

1.  SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. I. Taxonomy, fermentation, isolation and biological activities.

Authors:  K Kurosawa; K Takahashi; E Tsuda
Journal:  J Antibiot (Tokyo)       Date:  2001-07       Impact factor: 2.649

2.  Studies on the biomimetic synthesis of SNF4435 C and D.

Authors:  John E Moses; Jack E Baldwin; Rodolfo Marquez; Robert M Adlington; Andrew R Cowley
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

3.  Synthetic studies toward SNF4435 C and SNF4435 D.

Authors:  Christopher M Beaudry; Dirk Trauner
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

4.  "Endo" and "exo" bicyclo[4.2.0]-octadiene isomers from the electrocyclization of fully substituted tetraene models for SNF 4435C and D. control of stereochemistry by choice of a functionalized substituent.

Authors:  Kathlyn A Parker; Yeon-Hee Lim
Journal:  Org Lett       Date:  2004-01-22       Impact factor: 6.005

5.  Concise total synthesis and structure assignment of TAN-1085.

Authors:  Ken Ohmori; Keiji Mori; Yuji Ishikawa; Hideyuki Tsuruta; Shunsuke Kuwahara; Nobuyuki Harada; Keisuke Suzuki
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-14       Impact factor: 15.336

6.  DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085.

Authors:  Zeve R Akerling; Joseph E Norton; K N Houk
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

7.  SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. III. Immunosuppressive efficacy.

Authors:  Kazuhiko Kurosawa; Kosaku Takahashi; Nobuaki Fujise; Yasushi Yamashita; Naohiro Washida; Eisuke Tsuda
Journal:  J Antibiot (Tokyo)       Date:  2002-01       Impact factor: 2.649

8.  SNF4435C and D, novel immunosuppressants produced by a strain of Streptomyces spectabilis. II. Structure elucidation.

Authors:  K Takahashi; E Tsuda; K Kurosawa
Journal:  J Antibiot (Tokyo)       Date:  2001-07       Impact factor: 2.649

9.  Total synthesis and evaluation of phostriecin and key structural analogues.

Authors:  Christopher P Burke; Mark R Swingle; Richard E Honkanen; Dale L Boger
Journal:  J Org Chem       Date:  2010-07-29       Impact factor: 4.354

10.  Reversal of multidrug resistance by novel nitrophenyl pyrones, SNF4435C and D.

Authors:  K Kurosawa; K Takahashi; E Tsuda; A Tomida; T Tsuruo
Journal:  Jpn J Cancer Res       Date:  2001-11
View more
  4 in total

1.  Arabilin overcomes resistance to AR-targeted therapy.

Authors:  Takahiro Fujimaki; Shun Saito; Masaya Imoto
Journal:  J Antibiot (Tokyo)       Date:  2017-01-11       Impact factor: 2.649

2.  Total synthesis of kingianin A.

Authors:  Hee Nam Lim; Kathlyn A Parker
Journal:  Org Lett       Date:  2012-12-28       Impact factor: 6.005

3.  Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes.

Authors:  Ghina'a I Abu Deiab; Mohammed H Al-Huniti; I F Dempsey Hyatt; Emma E Nagy; Kristen E Gettys; Sommayah S Sayed; Christine M Joliat; Paige E Daniel; Rupa M Vummalaneni; Andrew T Morehead; Andrew L Sargent; Mitchell P Croatt
Journal:  Beilstein J Org Chem       Date:  2017-02-28       Impact factor: 2.883

4.  Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.

Authors:  Andrea Chaves-Pouso; Andrés M Álvarez-Constantino; Martín Fañanás-Mastral
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-21       Impact factor: 16.823
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.