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Literature DB >> 21126066

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

Abstract

A stereoselective synthesis of (+)-herboxidiene is described. The convergent synthesis utilized a Suzuki cross-coupling reaction to assemble the key segments. The synthesis of the functionalized tetrahydropyran ring utilized an Achmatowicz reaction as the key step. The synthesis of the C10-C19 segment was accomplished using Brown's crotylboration, asymmetric alkylation, and a stereoselective allylic chlorination reactions.

Entities: Chemical Disease Gene Species

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Year: 2010 PMID： 21126066 PMCID： PMC3075843 DOI： 10.1021/ol102549a

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

11 in total

1. Synthesis of simplified herboxidiene aromatic hybrids.

Authors: A J Edmunds; G Arnold; L Hagmann; R Schaffner; H Furlenmeier
Journal: Bioorg Med Chem Lett Date: 2000-06-19 Impact factor: 2.823

2. A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide.

Authors: K C Nicolaou; Anthony A Estrada; Mark Zak; Sang Hyup Lee; Brian S Safina
Journal: Angew Chem Int Ed Engl Date: 2005-02-18 Impact factor: 15.336

3. Asymmetric Synthesis of Calyculin C. 2. Synthesis of the C(26)-C(37) Fragment and Model Wittig Couplings.

Authors: Anthony K. Ogawa; John A. DeMattei; Gerard R. Scarlato; John E. Tellew; Lee S. Chong; Robert W. Armstrong
Journal: J Org Chem Date: 1996-09-06 Impact factor: 4.354

4. Total synthesis of herboxidiene/GEX 1A.

Authors: Yun Zhang; James S Panek
Journal: Org Lett Date: 2007-07-13 Impact factor: 6.005

5. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors: M Scholl; S Ding; C W Lee; R H Grubbs
Journal: Org Lett Date: 1999-09-23 Impact factor: 6.005

6. Trichostatin A and herboxidiene up-regulate the gene expression of low density lipoprotein receptor.

Authors: Y Koguchi; M Nishio; J Kotera; K Omori; T Ohnuki; S Komatsubara
Journal: J Antibiot (Tokyo) Date: 1997-11 Impact factor: 2.649

7. Synthesis and activity of ruthenium alkylidene complexes coordinated with phosphine and N-heterocyclic carbene ligands.

Authors: Tina M Trnka; John P Morgan; Melanie S Sanford; Thomas E Wilhelm; Matthias Scholl; Tae-Lim Choi; Sheng Ding; Michael W Day; Robert H Grubbs
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

8. Enantioselective preparation of the C1-C11 fragment of apoptolidin.

Authors: William D Paquette; Richard E Taylor
Journal: Org Lett Date: 2004-01-08 Impact factor: 6.005

9. Total synthesis of GEX1A.

Authors: Timothy J Murray; Craig J Forsyth
Journal: Org Lett Date: 2008-07-19 Impact factor: 6.005

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

23 in total

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

1. Synthesis of simplified herboxidiene aromatic hybrids.

2. A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide.

3. Asymmetric Synthesis of Calyculin C. 2. Synthesis of the C(26)-C(37) Fragment and Model Wittig Couplings.

4. Total synthesis of herboxidiene/GEX 1A.

5. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

6. Trichostatin A and herboxidiene up-regulate the gene expression of low density lipoprotein receptor.

7. Synthesis and activity of ruthenium alkylidene complexes coordinated with phosphine and N-heterocyclic carbene ligands.

8. Enantioselective preparation of the C1-C11 fragment of apoptolidin.

9. Total synthesis of GEX1A.

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

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

2. High-throughput single-molecule screen for small-molecule perturbation of splicing and transcription kinetics.

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

4. Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

5. Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.

6. Efficient, divergent synthesis of cryptophycin unit A analogues.

Review 7. A Challenging Pie to Splice: Drugging the Spliceosome.

Review 8. Modulating splicing with small molecular inhibitors of the spliceosome.

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

10. Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction.