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Literature DB >> 26466196

Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.

Yi Yang See¹, Aaron T Herrmann¹, Yoshinori Aihara¹, Phil S Baran¹.

Abstract

Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schönecker's Cu-mediated oxidation. This work shines new light onto this powerful C-H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members.

Entities: Chemical Disease Mutation Species

Mesh：

Substances：
Polymers
Pregnanes
Copper

Year: 2015 PMID： 26466196 PMCID： PMC5287264 DOI： 10.1021/jacs.5b09463

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

28 in total

1. Biomimetic hydroxylation of nonactivated CH2 groups with copper complexes and molecular oxygen.

Authors: Bruno Schönecker; Tatjana Zheldakova; Yong Liu; Manuela Kötteritzsch; Wolfgang Günther; Helmar Görls
Journal: Angew Chem Int Ed Engl Date: 2003-07-21 Impact factor: 15.336

Review 2. Dioxygen activation by copper, heme and non-heme iron enzymes: comparison of electronic structures and reactivities.

Authors: Andrea Decker; Edward I Solomon
Journal: Curr Opin Chem Biol Date: 2005-04 Impact factor: 8.822

3. Synthesis of cyclopamine using a biomimetic and diastereoselective approach.

Authors: Athanassios Giannis; Philipp Heretsch; Vasiliki Sarli; Anne Stössel
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

Review 4. The biochemical functions of ascorbic acid.

Authors: S Englard; S Seifter
Journal: Annu Rev Nutr Date: 1986 Impact factor: 11.848

5. Chemical Plausibility of Cu(III) with Biological Ligation in pMMO.

Authors: Cooper Citek; J Brannon Gary; Erik C Wasinger; T Daniel P Stack
Journal: J Am Chem Soc Date: 2015-05-28 Impact factor: 15.419

6. Intramolecular gamma-hydroxylations of nonactivated C-H bonds with copper complexes and molecular oxygen.

Authors: Bruno Schönecker; Tatjana Zheldakova; Corinna Lange; Wolfgang Günther; Helmar Görls; Martin Bohl
Journal: Chemistry Date: 2004-11-19 Impact factor: 5.236

7. The first conjugate addition reaction of terminal alkynes catalytic in copper: conjugate addition of alkynes in water.

Authors: Thomas F Knöpfel; Erick M Carreira
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

8. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

Authors: Ke Chen; Jeremy M Richter; Phil S Baran
Journal: J Am Chem Soc Date: 2008-05-16 Impact factor: 15.419

9. Academia-industry symbiosis in organic chemistry.

Authors: Quentin Michaudel; Yoshihiro Ishihara; Phil S Baran
Journal: Acc Chem Res Date: 2015-02-23 Impact factor: 22.384

10. C-H-Functionalization logic guides the synthesis of a carbacyclopamine analog.

Authors: Sebastian Rabe; Johann Moschner; Marina Bantzi; Philipp Heretsch; Athanassios Giannis
Journal: Beilstein J Org Chem Date: 2014-07-09 Impact factor: 2.883

21 in total

1. Chemical synthesis of 7-oxygenated 12α-hydroxy steroid derivatives to enable the biochemical characterization of cytochrome P450 8B1, the oxysterol 12α-hydroxylase enzyme implicated in cardiovascular health and obesity.

Authors: Samuel D Offei; Hadi D Arman; Mirza Oais Baig; Lazaro S Chavez; Carlos A Paladini; Francis K Yoshimoto
Journal: Steroids Date: 2018-11-03 Impact factor: 2.668

2. Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

Authors: Hem Raj Khatri; Bijay Bhattarai; Will Kaplan; Zhongzheng Li; Marcus John Curtis Long; Yimon Aye; Pavel Nagorny
Journal: J Am Chem Soc Date: 2019-03-14 Impact factor: 15.419

3. Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors: Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal: European J Org Chem Date: 2020-01-01

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.

1. Biomimetic hydroxylation of nonactivated CH2 groups with copper complexes and molecular oxygen.

Review 2. Dioxygen activation by copper, heme and non-heme iron enzymes: comparison of electronic structures and reactivities.

3. Synthesis of cyclopamine using a biomimetic and diastereoselective approach.

Review 4. The biochemical functions of ascorbic acid.

5. Chemical Plausibility of Cu(III) with Biological Ligation in pMMO.

6. Intramolecular gamma-hydroxylations of nonactivated C-H bonds with copper complexes and molecular oxygen.

7. The first conjugate addition reaction of terminal alkynes catalytic in copper: conjugate addition of alkynes in water.

8. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

9. Academia-industry symbiosis in organic chemistry.

10. C-H-Functionalization logic guides the synthesis of a carbacyclopamine analog.

1. Chemical synthesis of 7-oxygenated 12α-hydroxy steroid derivatives to enable the biochemical characterization of cytochrome P450 8B1, the oxysterol 12α-hydroxylase enzyme implicated in cardiovascular health and obesity.

2. Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

3. Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

5. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

6. Methylene C(sp³)-H Arylation of Aliphatic Ketones Using a Transient Directing Group.

7. Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions.

8. Decoding the Mechanism of Intramolecular Cu-Directed Hydroxylation of sp³ C-H Bonds.

Review 9. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

10. Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Review 2. Dioxygen activation by copper, heme and non-heme iron enzymes: comparison of electronic structures and reactivities.

Review 4. The biochemical functions of ascorbic acid.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 9. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.