scholarly journals A TOTAL SYNTHESIS OF (±)-WIDDROL. SYNTHETIC APPLICATION OF THE FORMAL BRIDGEHEAD SUBSTITUTION OF 1-METHOXYBICYCLO[3.2.2]NON-6-EN-2-ONES WITH ALKYL GROUPS

1986 ◽  
Vol 15 (4) ◽  
pp. 609-612 ◽  
Author(s):  
Tadao Uyehara ◽  
Jun-ichi Yamada ◽  
Toshiaki Furuta ◽  
Tadahiro Kato
Keyword(s):  
Total Synthesis ◽  
Alkyl Groups ◽  
Synthetic Application

Endohexosaminidase-catalyzed synthesis of glycopeptides and proteins

2013 ◽  
Vol 85 (9) ◽  
pp. 1847-1863 ◽  
Author(s):  
Antony J. Fairbanks
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Natural Sources ◽  
Glcnac Residue ◽  
Amino Acid Peptide ◽  
Ready Access ◽  
Synthetic Application

The synthetic application of endohexosaminidase enzymes (e.g., Endo A, Endo M, Endo D) promises to allow ready access to a wide variety of defined homogeneous glycoproteins and glycopeptides. The use ofN-glycan oligosaccharides that are activated at the reducing terminus as oxazolines allows their high-yielding attachment to almost any amino acid, peptide, or protein that contains a GlcNAc residue as an acceptor. A wide variety of oxazoline donors are readily available, either by total synthesis or by isolation of the corresponding oligosaccharide from natural sources and then conversion to the oxazoline in water. The synthetic potential of the enzymes is particularly augmented by the production of mutant glycosynthases, the use of which allows the synthesis of a wide variety of glycopeptides and glycoproteins bearing defined homogeneousN-glycan structures.

scholarly journals Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C−H/C−H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

2020 ◽  
Author(s):  
Zhe Zhuang ◽  
Alastair Herron ◽  
Shuang Liu ◽  
jin-quan yu
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Phenylacetic Acid ◽  
Coupling Reaction ◽  
Pivalic Acid ◽  
Coupling Reactions ◽  
Amino Acid Ligand ◽  
Acid Ligand ◽  
Rapid Construction ◽  
Synthetic Application

The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp<sup>3</sup>)−H/C(sp<sup>2</sup>)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-<i>N</i>-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.

scholarly journals Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C−H/C−H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

2020 ◽  
Author(s):  
Zhe Zhuang ◽  
Alastair Herron ◽  
Shuang Liu ◽  
jin-quan yu
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Phenylacetic Acid ◽  
Coupling Reaction ◽  
Pivalic Acid ◽  
Coupling Reactions ◽  
Amino Acid Ligand ◽  
Acid Ligand ◽  
Rapid Construction ◽  
Synthetic Application

The development of practical C−H/C−H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C−C bonds. Herein, we report a cyclative C(sp<sup>3</sup>)−H/C(sp<sup>2</sup>)−H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-<i>N</i>-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na<sub>2</sub>CO<sub>3</sub>·1.5H<sub>2</sub>O<sub>2</sub>) as the sole oxidant, generating water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, could be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through the sequential functionalizations of four C−H bonds.

Heteroannulation enabled by a bimetallic Rh(iii)/Ag(i) relay catalysis: application in the total synthesis of aristolactam BII

2017 ◽  
Vol 53 (41) ◽  
pp. 5665-5668 ◽  
Author(s):  
Wei-Wei Ji ◽  
E. Lin ◽  
Qingjiang Li ◽  
Honggen Wang
Keyword(s):  
Total Synthesis ◽  
Synthetic Application

A Rh(iii)/Ag(i) relay catalysis allowed the construction of 3-alkylidene isoindolinones and 3-alkylidene isobenzofuranones. The synthetic application in the total synthesis was accomplished.

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