Acid-Catalyzed Rearrangement of Epoxy Alcohol Derivatives Having the Electron-Withdrawing Protective Groups (Acyl or Sulfonyl): Asymmetric Synthesis of Chiral Quaternary Carbon and Spiro Centers and Its Application to Natural Products Synthesis

ChemInform ◽  
2003 ◽  
Vol 34 (25) ◽  
Author(s):  
Hiromichi Fujioka ◽  
Yutaka Yoshida ◽  
Yasuyuki Kita
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Quaternary Carbon ◽  
Epoxy Alcohol ◽  
Protective Groups ◽  
Acid Catalyzed ◽  
Natural Products Synthesis

Tiacumicin B: An Antibiotic of Prime Importance and a Natural Product with an Inspiring Complex Structure

Synthesis ◽  
2018 ◽  
Vol 50 (21) ◽  
pp. 4189-4200 ◽  
Author(s):  
Emmanuel Roulland
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Complex Structure ◽  
Short Review ◽  
Molecular Structures ◽  
Protective Groups ◽  
Natural Products Synthesis

This short review aims at decrypting and analyzing the various strategies used for the synthesis of tiacumicin B. Natural products synthesis is a way for organic chemists to express inventiveness, intellectual dexterity, and elegance in strategy of synthesis. Some molecular structures are more inspiring than others; and if like tiacumicin B, the architectural challenge meets high biological and medicinal interest, the molecule can then attract the attention of many groups of synthetic chemists.1 Introduction2 The Strategic Challenges of this Total Synthesis3 Construction of the C1–C5 Region4 Construction of the C14–C19 Region5 Construction of the C5–C12 Region6 Construction of the C12–C15 Diene Motif7 Macrocyclization8 Synthesis of the Rhamnosyl Donor9 Synthesis of the Noviosyl Donor and Glycosylation10 The Recurrent Problems Caused by Protective Groups11 Conclusion

Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis

2021 ◽  
Author(s):  
Nengzhong Wang ◽  
Zugen Wu ◽  
Junjie Wang ◽  
Nisar Ullah ◽  
Yixin Lu
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Natural Products Synthesis

A comprehensive and updated summary of asymmetric organocatalytic annulation reactions is presented; in particular, the applications of these annulation strategies to natural products synthesis are highlighted.

Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction

2000 ◽  
Vol 11 (12) ◽  
pp. 2509-2523 ◽  
Author(s):  
Renée Paugam ◽  
Emmanuelle Valenciennes ◽  
Linda Le Coz-Bardol ◽  
Jean-Christophe Garde ◽  
Lya Wartski ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Acid Catalyzed

Efficient Synthesis of Propargylic Ethers under the DBU Conditions and Its Application to Natural Products Synthesis.

ChemInform ◽  
2007 ◽  
Vol 38 (28) ◽  
Author(s):  
Tadashi Yokoyama ◽  
Noriki Kutsumura ◽  
Tadaaki Ohgiya ◽  
Shigeru Nishiyama
Keyword(s):  
Natural Products ◽  
Efficient Synthesis ◽  
Natural Products Synthesis

Central–axial–central chirality transfer: asymmetric synthesis of highly substituted indenes bearing a stereogenic quaternary carbon center from optically active propargyl alcohols

2015 ◽  
Vol 51 (2) ◽  
pp. 380-383 ◽  
Author(s):  
Masahiro Egi ◽  
Kaori Shimizu ◽  
Marin Kamiya ◽  
Yuya Ota ◽  
Shuji Akai
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Quaternary Carbon ◽  
Chirality Transfer ◽  
Propargyl Alcohols

An asymmetric synthesis of highly substituted indenes has been developed via the central–axial–central chirality transfer from optically active propargyl alcohols.

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