scholarly journals Recent Applications and Developments of Organic Azides in Total Synthesis of Natural Products

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Hiroki Tanimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Chemical Biology ◽  
Organic Reactions ◽  
Bioactive Molecules ◽  
Preparation Methods ◽  
Organic Azides ◽  
Agricultural Areas

Organic azides have been exploited since their discovery because of their high reactivities. Various organic reactions using azides have been synthetically applied in chemical biology pharmaceuticals medicinal and agricultural areas. In this review we present some recent applications and developments of organic azides in the total synthesis of natural products (mostly within five years) especially alkaloids. We focus not only on application examples of organic azides but also show their preparation methods including recently reported procedures concerning their decomposing and reducing methods in the syntheses of bioactive molecules.

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.

Enzyme alchemy: cell-free synthetic biochemistry for natural products

2019 ◽  
Vol 3 (5) ◽  
pp. 529-535 ◽  
Author(s):  
Simon J. Moore
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Living Cell ◽  
Chemical Biology ◽  
Low Cost ◽  
Challenges And Opportunities ◽  
Whole Cell Biotransformation ◽  
Synthesis Routes ◽  
Novel Antibiotics

Cell-free synthetic biochemistry aims to engineer chemical biology by exploiting biosynthetic dexterity outside of the constraints of a living cell. One particular use is for making natural products, where cell-free systems have initially demonstrated feasibility in the biosynthesis of a range of complex natural products classes. This has shown key advantages over total synthesis, such as increased yield, enhanced regioselectivity, use of reduced temperatures and less reaction steps. Uniquely, cell-free synthetic biochemistry represents a new area that seeks to advance upon these efforts and is particularly useful for defining novel synthetic pathways to replace natural routes and optimising the production of complex natural product targets from low-cost precursors. Key challenges and opportunities will include finding solutions to scaled-up cell-free biosynthesis, as well as the targeting of high value and toxic natural products that remain challenging to make either through whole-cell biotransformation platforms or total synthesis routes. Although underexplored, cell-free synthetic biochemistry could also be used to develop ‘non-natural’ natural products or so-called xenobiotics for novel antibiotics and drugs, which can be difficult to engineer directly within a living cell.

Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Synthesis ◽  
2017 ◽  
Vol 49 (22) ◽  
pp. 4899-4916 ◽  
Author(s):  
Rongbiao Tong ◽  
Zhihong Zhang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Michael Addition ◽  
Synthetic Methods ◽  
Bioactive Molecules ◽  
Structural Motif ◽  
Heck Cyclization ◽  
Epoxide Opening ◽  
Oxocarbenium Ion ◽  
Synthetic Approaches

Being different from 2,6-cis-tetrahydropyrans (2,6-cis-THPs), the corresponding 2,6-trans-THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6-trans-THP subunit has led to the development of many efficient synthetic approaches to access 2,6-trans-THPs. This review summarizes various synthetic methods reported for this structural motif and/or related applications in the total synthesis of natural products.1 Introduction2 Nucleophilic Addition to an Oxocarbenium Ion (Strategy A)3 Intramolecular Oxa-Michael Addition (Strategy B)4 Intermolecular Michael Addition to Dihydropyranones (Strategy A)5 The Heck–Matsuda (Strategy A) Reaction and Oxa-Heck Cyclization (Strategy B)6 Intramolecular SN2 Substitution and Epoxide Opening (Strategy B)7 Miscellaneous Methods8 Conclusion and Outlook

scholarly journals Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3412 ◽  
Author(s):  
Zhonglei Wang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Secondary Amine ◽  
Bioactive Molecules ◽  
Secondary Amines ◽  
Asymmetric Total Synthesis ◽  
Bioactive Natural Products ◽  
Unsaturated Aldehydes ◽  
Target Molecules ◽  
Catalyzed Reactions

Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due to their extensive application of organocatalysis in the total synthesis of bioactive molecules and some of them have been used in the industrial synthesis of drugs have attracted increasing interests from chemists. Among the chiral organocatalysts, chiral secondary amines (MacMillan’s catalyst and Jorgensen’s catalyst) have been especially considered attractive strategies because of their impressive efficiency. Herein, we outline advances in the asymmetric total synthesis of natural products and relevant drugs by using the strategy of chiral secondary amine catalyzed reactions of α,β-unsaturated aldehydes in the last eighteen years.

scholarly journals Developments of Corey-Chaykovsky in Organic Reactions and Total Synthesis of Natural Products

2016 ◽  
Vol 13 (3) ◽  
pp. 308-333 ◽  
Author(s):  
Majid M. Heravi ◽  
Shima Asadi ◽  
Niousha Nazari ◽  
Boshra Malekzadeh Lashkariani
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Reactions

scholarly journals Conquering peaks and illuminating depths: developing stereocontrolled organic reactions to unlock nature's macrolide treasure trove

2021 ◽  
Vol 57 (26) ◽  
pp. 3171-3189
Author(s):  
Nelson Y. S. Lam ◽  
Tegan P. Stockdale ◽  
Matthew J. Anketell ◽  
Ian Paterson
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Reactions ◽  
Personal Perspective ◽  
Treasure Trove ◽  
Representative Selection ◽  
Selection Of

Exemplified by a representative selection of macrolide natural products, this personal perspective reflects on the trials, tribulations and serendipitous discoveries experienced in pursuit of their total synthesis exploiting aldol methodology.

Application of Dess-Martin oxidation in total synthesis of natural products

2020 ◽  
Vol 17 ◽  
Author(s):  
Majid M. Heravi ◽  
Tayebe Momeni ◽  
Vahideh Zadsirjan ◽  
Leila Mohammadi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Selective Oxidation ◽  
Secondary Alcohols ◽  
Aldehydes And Ketones

: Dess–Martin periodinane (DMP), is a commercially available chemical, frequently being utilized as a mild oxidative agent for the selective oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. DMP shows several merits over other common oxidative agent such as chromium- and DMSO-based oxidants, thus it is habitually employed in the total synthesis of natural products. In this review, we try to underscore the applications of DMP as an effective oxidant in an appropriate step (steps) in the multistep total synthesis of natural products.

Total synthesis: the structural confirmation of natural products

2021 ◽  
Vol 57 (27) ◽  
pp. 3307-3322
Author(s):  
Debobrata Paul ◽  
Ashis Kundu ◽  
Sanu Saha ◽  
Rajib Kumar Goswami
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Feature Article

This feature article highlights total synthesis as one of the reliable tools for the structural confirmation of natural products.

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