C2-Symmetric Pyrrolidines Derived from Tartaric Acids: Versatile Chiral Building Blocks for Total Synthesis, Catalyst Design, Supramolecular and Medicinal Chemistry

2009 ◽  
Vol 6 (1) ◽  
pp. 38-53 ◽  
Author(s):  
Andreas Blum ◽  
Wibke Diederich
Keyword(s):  
Total Synthesis ◽  
Medicinal Chemistry ◽  
Building Blocks ◽  
Catalyst Design ◽  
Tartaric Acids

Cascade CuH-Catalyzed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products

2019 ◽  
Author(s):  
De-Wei Gao ◽  
Yang Gao ◽  
Huiling Shao ◽  
Tian-Zhang Qiao ◽  
Xin Wang ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Proteasome Inhibitors ◽  
Building Blocks ◽  
Unique Role ◽  
Efficient Strategy ◽  
Carbon Centers ◽  
Rapid Access ◽  
Cascade Catalysis ◽  
Privileged Scaffolds

Enantioenriched <i>α</i>-aminoboronic acids play a unique role in medicinal chemistry and have emerged as privileged pharmacophores in proteasome inhibitors. Additionally, they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asymmetric alkene hydrofunctionalization has become a powerful tool to construct stereogenic carbon centers. In contrast, applying CuH cascade catalysis to achieve reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, we report an efficient strategy to synthesize <i>α</i>-aminoboronates <i>via </i>CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product in favor of alternative homodifunctionalized, 1,2-heterodifunctionalized, or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity.<br>

scholarly journals Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 720
Author(s):  
Satomi Niwayama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Organic Compounds ◽  
Recent Progress ◽  
Aqueous Media ◽  
Building Blocks ◽  
Organic Reactions ◽  
Environmentally Benign ◽  
Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

Total Synthesis of Woodrosin I. Part 1. Preparation of the Building Blocks and Evaluation of the Glycosylation Strategy.

ChemInform ◽  
2003 ◽  
Vol 34 (18) ◽  
Author(s):  
Alois Fuerstner ◽  
Fabien Jeanjean ◽  
Patrick Razon ◽  
Conny Wirtz ◽  
Richard Mynott
Keyword(s):  
Total Synthesis ◽  
Building Blocks

scholarly journals Janus All‐Cis 2,3,4,5,6‐Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry

2021 ◽  
Author(s):  
Joshua L. Clark ◽  
Rifahath M. Neyyappadath ◽  
Cihang Yu ◽  
Alexandra M. Z. Slawin ◽  
David B. Cordes ◽  
...  
Keyword(s):  
Medicinal Chemistry ◽  
Building Blocks

Stereocontrolled construction of key building blocks for the total synthesis of amphoteronolide B and amphotericin B

1987 ◽  
Vol 109 (7) ◽  
pp. 2205-2208 ◽  
Author(s):  
Kyriacos C. Nicolaou ◽  
R. A. Daines ◽  
J. Uenishi ◽  
W. S. Li ◽  
D. P. Papahatjis ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Amphotericin B ◽  
Building Blocks

ChemInform Abstract: Stereocontrolled Construction of Key Building Blocks for the Total Synthesis of Amphoteronolide B and Amphotericin B.

ChemInform ◽  
1987 ◽  
Vol 18 (33) ◽  
Author(s):  
K. C. NICOLAOU ◽  
R. A. DAINES ◽  
J. UENISHI ◽  
W. S. LI ◽  
D. P. PAPAHATJIS ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Amphotericin B ◽  
Building Blocks

Emerging building blocks for medicinal chemistry: recent synthetic advances

2021 ◽  
Author(s):  
Oleksandr O Grygorenko ◽  
Dmitriy M. Volochnyuk ◽  
Bohdan V. Vashchenko
Keyword(s):  
Medicinal Chemistry ◽  
Building Blocks
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