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Literature DB >> 18642829

Total synthesis of GEX1A.

Abstract

An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 ( 1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18642829 DOI： 10.1021/ol800902g

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

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Cited

10 in total

1. Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment.

Authors: Yusuke Yoshikawa; Airi Ishibashi; Tsunayoshi Takehara; Takeyuki Suzuki; Kenichi Murai; Yasufumi Kaneda; Keisuke Nimura; Mitsuhiro Arisawa
Journal: ACS Med Chem Lett Date: 2020-05-01 Impact factor: 4.345

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

5. 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

6. 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

Total synthesis of GEX1A.

1. Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment.

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

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

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

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

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

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

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

9. Multifunctional organoboron compounds for scalable natural product synthesis.

Review 10. Microbial and Natural Metabolites That Inhibit Splicing: A Powerful Alternative for Cancer Treatment.