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Literature DB >> 30207731

Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling.

Houng Kang¹, Carilyn Torruellas², Jinchu Liu³, Marisa C Kozlowski¹.

Abstract

The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key step, enabled generation of the axial chirality.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2018 PMID： 30207731 PMCID： PMC6174078 DOI： 10.1021/acs.orglett.8b02183

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

8 in total

1. Synthesis of azaphilones and related molecules by employing cycloisomerization of o-alkynylbenzaldehydes.

Authors: Jianglong Zhu; Andrew R Germain; John A Porco
Journal: Angew Chem Int Ed Engl Date: 2004-02-27 Impact factor: 15.336

2. Total synthesis of (+)-brefeldin A.

Authors: Yikang Wu; Jian Gao
Journal: Org Lett Date: 2008-03-14 Impact factor: 6.005

3. Copper-catalyzed halogen exchange in aryl halides: an aromatic Finkelstein reaction.

Authors: Artis Klapars; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2002-12-18 Impact factor: 15.419

4. Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation.

Authors: Benjamin M Partridge; John F Hartwig
Journal: Org Lett Date: 2012-12-20 Impact factor: 6.005

5. One-pot synthesis of highly substituted 4-acetonylindoles via sequential dearomatization and silver-catalyzed domino reaction.

Authors: Xin Feng; Huiqing Wang; Bo Yang; Renhua Fan
Journal: Org Lett Date: 2014-06-25 Impact factor: 6.005

6. Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation.

Authors: Jaclyn M Murphy; Xuebin Liao; John F Hartwig
Journal: J Am Chem Soc Date: 2007-11-21 Impact factor: 15.419

7. Chaetoglobins A and B, two unusual alkaloids from endophytic Chaetomium globosum culture.

Authors: Hui Ming Ge; Wei Yun Zhang; Gang Ding; Patchareenart Saparpakorn; Yong Chun Song; Supa Hannongbua; Ren Xiang Tan
Journal: Chem Commun (Camb) Date: 2008-10-10 Impact factor: 6.222

8. Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles.

Authors: Houng Kang; Young Eun Lee; Peddiahgari Vasu Govardhana Reddy; Sangeeta Dey; Scott E Allen; Kyle A Niederer; Paul Sung; Kirsten Hewitt; Carilyn Torruellas; Madison R Herling; Marisa C Kozlowski
Journal: Org Lett Date: 2017-10-12 Impact factor: 6.005

8 in total

6 in total

Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling.

1. Synthesis of azaphilones and related molecules by employing cycloisomerization of o-alkynylbenzaldehydes.

2. Total synthesis of (+)-brefeldin A.

3. Copper-catalyzed halogen exchange in aryl halides: an aromatic Finkelstein reaction.

4. Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation.

5. One-pot synthesis of highly substituted 4-acetonylindoles via sequential dearomatization and silver-catalyzed domino reaction.

6. Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation.

7. Chaetoglobins A and B, two unusual alkaloids from endophytic Chaetomium globosum culture.

8. Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles.

1. Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C-C and C-O Coupling.

2. Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.

3. Catalytic Oxidative Coupling of Phenols and Related Compounds.

4. Diastereoselective Synthesis of Benzoxanthenones.

Review 5. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

Review 6. Recent advances in the chemistry and biology of azaphilones.