Literature DB >> 17629295

Total synthesis of herboxidiene/GEX 1A.

Yun Zhang1, James S Panek.   

Abstract

A convergent enantioselective synthesis of herboxidiene/GEX 1A (1) is described that features a double stereodifferentiating crotylation, [4 + 2] annulation, and a silicon-based sp2-sp2 cross-coupling to assemble the conjugated diene.

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Year:  2007        PMID： 17629295      PMCID： PMC3164305          DOI： 10.1021/ol701427k

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


  10 in total

1.  Dinuclear asymmetric Zn aldol additions: formal asymmetric synthesis of fostriecin.

Authors:  Barry M Trost; Mathias U Frederiksen; Julien P N Papillon; Paul E Harrington; Seunghoon Shin; Brock T Shireman
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

2.  Stereocontrolled [4+2]-annulation accessing dihydropyrans: synthesis of the C1a-C10 fragment of kendomycin.

Authors:  Jason T Lowe; James S Panek
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

3.  A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions.

Authors:  Scott E Denmark; Luc Neuville; Matthew E L Christy; Steven A Tymonko
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

4.  Sequential silylcarbocyclization/silicon-based cross-coupling reactions.

Authors:  Scott E Denmark; Jack Hung-Chang Liu
Journal:  J Am Chem Soc       Date:  2007-03-03       Impact factor: 15.419

5.  Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.

Authors:  K Takai; M Tagashira; T Kuroda; K Oshima; K Utimoto; H Nozaki
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

6.  A stereodivergent approach to chiral nonracemic N-protected alpha,alpha-dialkylated amino acids.

Authors:  Claude Spino; Cédrickx Godbout; Cédrickx Gobdout
Journal:  J Am Chem Soc       Date:  2003-10-08       Impact factor: 15.419

7.  Fluoride-promoted cross-coupling reactions of alkenylsilanols. Elucidation of the mechanism through spectroscopic and kinetic analysis.

Authors:  Scott E Denmark; Ramzi F Sweis; Daniel Wehrli
Journal:  J Am Chem Soc       Date:  2004-04-21       Impact factor: 15.419

8.  Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality.

Authors:  Barry M Trost; Michelle R Machacek; Zachary T Ball
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

9.  GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. II. The effects on cell cycle progression and gene expression.

Authors:  Yasushi Sakai; Tetsuya Tsujita; Tadakazu Akiyama; Tatsuhiko Yoshida; Tamio Mizukami; Shiro Akinaga; Sueharu Horinouchi; Minoru Yoshida; Tetsuo Yoshida
Journal:  J Antibiot (Tokyo)       Date:  2002-10       Impact factor: 2.649

10.  GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. I. Taxonomy, production, isolation, physicochemical properties and biological activities.

Authors:  Yasushi Sakai; Tetsuo Yoshida; Keiko Ochiai; Youichi Uosaki; Yutaka Saitoh; Futoshi Tanaka; Tadakazu Akiyama; Shiro Akinaga; Tamio Mizukami
Journal:  J Antibiot (Tokyo)       Date:  2002-10       Impact factor: 2.649
  10 in total
  11 in total

1.  Identification of the herboxidiene biosynthetic gene cluster in Streptomyces chromofuscus ATCC 49982.

Authors:  Lei Shao; Jiachen Zi; Jia Zeng; Jixun Zhan
Journal:  Appl Environ Microbiol       Date:  2012-01-13       Impact factor: 4.792

2.  A stereoselective synthesis of (+)-herboxidiene/GEX1A.

Authors:  Arun K Ghosh; Jianfeng Li
Journal:  Org Lett       Date:  2010-12-02       Impact factor: 6.005

3.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

4.  Design, synthesis and in vitro splicing inhibition of desmethyl and carba-derivatives of herboxidiene.

Authors:  Arun K Ghosh; Kai Lv; Nianchun Ma; Emilio L Cárdenas; Kerstin A Effenberger; Melissa S Jurica
Journal:  Org Biomol Chem       Date:  2016-05-18       Impact factor: 3.876

Review 5.  Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin.

Authors:  Zhenlei Song; Andrew G Lohse; Richard P Hsung
Journal:  Nat Prod Rep       Date:  2009-04       Impact factor: 13.423

6.  GEX1A, a Polyketide from Streptomyces chromofuscus, Corrects the Cellular Defects Associated with Niemann-Pick Type C1 in Human Fibroblasts.

Authors:  Eve A Granatosky; Nina DiPrimio; Jarred R E Pickering; D Cole Stevens; Ethan O Perlstein; Richard E Taylor
Journal:  J Nat Prod       Date:  2018-09-06       Impact factor: 4.050

7.  Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives.

Authors:  Chandraiah Lagisetti; Maria V Yermolina; Lalit Kumar Sharma; Gustavo Palacios; Brett J Prigaro; Thomas R Webb
Journal:  ACS Chem Biol       Date:  2013-12-30       Impact factor: 5.100

8.  Synthesis of a 35-member stereoisomer library of bistramide A: evaluation of effects on actin state, cell cycle and tumor cell growth.

Authors:  Iwona E Wrona; Jason T Lowe; Thomas J Turbyville; Tanya R Johnson; Julien Beignet; John A Beutler; James S Panek
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

9.  Design and synthesis of herboxidiene derivatives that potently inhibit in vitro splicing.

Authors:  Arun K Ghosh; Srinivasa Rao Allu; Guddeti Chandrashekar Reddy; Adriana Gamboa Lopez; Patricia Mendez; Melissa S Jurica
Journal:  Org Biomol Chem       Date:  2021-02-18       Impact factor: 3.876

10.  Total synthesis of GEX1Q1, assignment of C-5 stereoconfiguration and evaluation of spliceosome inhibitory activity.

Authors:  Arun K Ghosh; Nianchun Ma; Kerstin A Effenberger; Melissa S Jurica
Journal:  Org Lett       Date:  2014-05-28       Impact factor: 6.005
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