Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks

2009 ◽  
Vol 38 (11) ◽  
pp. 3222 ◽  
Author(s):  
Corinna S. Schindler ◽  
Erick M. Carreira
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Building Blocks ◽  
Rapid Formation

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.

Dimethylformamide Acetals and Bredereck’s Reagent as Building Blocks in Natural Products Total Synthesis

2020 ◽  
Vol 17 (1) ◽  
pp. 47-66
Author(s):  
Franz Bracher
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alkylating Agents ◽  
Building Blocks ◽  
Methyl Groups ◽  
Open Chain ◽  
Enol Ethers ◽  
Condensation Products ◽  
Condensation Reactions

Dimethylformamide acetals and Bredereck’s reagent (tert-butoxy-bis(dimethylamino) methane) are versatile C1 building blocks due to their ability to undergo condensation reactions with CH-acidic methyl and methylene moieties. Subsequent modulation of the resulting condensation products enables the preparation of open-chain products like aldehydes, ketones, enones, enol ethers, methyl groups, and, most important in alkaloid total synthesis, the annulation of heterocyclic rings like pyridines, pyridine-N-oxides, bromopyridines, aminopyridines, aminopyrimidines, pyrroles and chromenones. In certain cases, these reagents can act as alkylating agents. The applications of these building blocks in natural products total synthesis are reviewed here.

scholarly journals Syntheses of Cyclomarins – Interesting Marine Natural Products with Distinct Mode of Action towards Malaria and Tuberculosis

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 107-121 ◽  
Author(s):  
Alexander Kiefer ◽  
Uli Kazmaier
Keyword(s):  
Amino Acids ◽  
Plasmodium Falciparum ◽  
Natural Products ◽  
Total Synthesis ◽  
Building Blocks ◽  
Distinct Mode ◽  
Unusual Amino Acids ◽  
Caseinolytic Protease ◽  
A Subunit ◽  
Cyclomarin A

The cyclomarins are cyclic heptapeptides from marine streptomycetes containing four rather unusual amino acids. Interestingly, the cyclomarins address two completely different targets: ClpC1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Aase of Plasmodium falciparum. Therefore, the cyclomarins are interesting lead structures for the development of drugs targeting tuberculosis and malaria. As a result, several synthetic protocols towards the synthesis of these unusual building blocks as well as the natural products themselves have been developed, which will be discussed in this review.1 Introduction2 Synthesis of the Building Blocks3 Total Synthesis of Cyclomarin C by Yao and Co-workers4 Total Synthesis of Cyclomarin A and C by Barbie and Kazmaier5 Conclusion

scholarly journals Making natural products from renewable feedstocks: back to the roots?

2020 ◽  
Vol 37 (3) ◽  
pp. 380-424 ◽  
Author(s):  
Jonas Kühlborn ◽  
Jonathan Groß ◽  
Till Opatz
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Building Blocks ◽  
Renewable Feedstocks

This review highlights the utilization of biomass-derived building blocks in the total synthesis of natural products.

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