Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Exo-selective reductive macrocyclization of ynals.

Literature DB >> 25746060

Exo-selective reductive macrocyclization of ynals.

Hengbin Wang¹, Solymar Negretti¹, Allison R Knauff¹, John Montgomery¹.

Abstract

A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2015 PMID： 25746060 PMCID： PMC4381747 DOI： 10.1021/acs.orglett.5b00381

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

40 in total

1. Copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide and hydrosilanes.

Authors: Tetsuaki Fujihara; Tinghua Xu; Kazuhiko Semba; Jun Terao; Yasushi Tsuji
Journal: Angew Chem Int Ed Engl Date: 2011-01-10 Impact factor: 15.336

Review 2. Macrocyclic drugs and clinical candidates: what can medicinal chemists learn from their properties?

Authors: Fabrizio Giordanetto; Jan Kihlberg
Journal: J Med Chem Date: 2013-09-17 Impact factor: 7.446

Review 3. Catalytic selective synthesis.

Authors: Jessada Mahatthananchai; Aaron M Dumas; Jeffrey W Bode
Journal: Angew Chem Int Ed Engl Date: 2012-09-25 Impact factor: 15.336

Review 4. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.

Authors: Eric Marsault; Mark L Peterson
Journal: J Med Chem Date: 2011-03-07 Impact factor: 7.446

5. A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors: Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal: J Am Chem Soc Date: 2010-05-12 Impact factor: 15.419

6. Ligand-controlled regiodivergent nickel-catalyzed annulation of pyridones.

Authors: Pavel A Donets; Nicolai Cramer
Journal: Angew Chem Int Ed Engl Date: 2014-11-06 Impact factor: 15.336

7. Enantioselective synthesis of (-)-terpestacin and structural revision of siccanol using catalytic stereoselective fragment couplings and macrocyclizations.

Authors: Johann Chan; Timothy F Jamison
Journal: J Am Chem Soc Date: 2004-09-01 Impact factor: 15.419

8. Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations.

Authors: Yu Bai; Dexter C Davis; Mingji Dai
Journal: Angew Chem Int Ed Engl Date: 2014-05-13 Impact factor: 15.336

Exo-selective reductive macrocyclization of ynals.

1. Copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide and hydrosilanes.

Review 2. Macrocyclic drugs and clinical candidates: what can medicinal chemists learn from their properties?

Review 3. Catalytic selective synthesis.

Review 4. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.

5. A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

6. Ligand-controlled regiodivergent nickel-catalyzed annulation of pyridones.

7. Enantioselective synthesis of (-)-terpestacin and structural revision of siccanol using catalytic stereoselective fragment couplings and macrocyclizations.

8. Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations.

9. Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.

Review 10. Macrocyclic drugs and synthetic methodologies toward macrocycles.

1. NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

2. Mechanistic Basis for Regioselection and Regiodivergence in Nickel-Catalyzed Reductive Couplings.

3. Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

4. A modular and enantioselective synthesis of the pleuromutilin antibiotics.

5. Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

6. Synthesis of Diverse 11- and 12-Membered Macrolactones from a Common Linear Substrate Using a Single Biocatalyst.