Advances in catalytic and protecting-group-free total synthesis of natural products: a recent update

2020 ◽  
Vol 56 (61) ◽  
pp. 8569-8590 ◽  
Author(s):  
Rodney A. Fernandes ◽  
Praveen Kumar ◽  
Priyanka Choudhary
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Protecting Group ◽  
Feature Article ◽  
Total Syntheses

This feature article highlights the recently achieved efficient total syntheses of many natural products based on catalytic steps and protecting-group-free strategies, leading to overall economy and efficiency in synthesis.

scholarly journals Recent Chemical Methodology Advances in the Total Synthesis of Meroterpenoids

2021 ◽  
Vol 68 (2) ◽  
pp. 247-267
Author(s):  
Jan Petrovčič ◽  
Chad Nicholas Ungarean ◽  
David Sarlah
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Synthesis ◽  
Feature Article ◽  
Total Syntheses ◽  
Synthetic Organic Chemistry ◽  
Synthetic Studies

Heterogeneity of meroterpenoids arising from their dual biosynthetic origins is constantly provoking synthetic chemists to utilize their ingenuity and revise their retrosynthetic logic. By studying recent publications on meroterpenoid synthesis,tremendous advances in the field of synthetic organic chemistry can be witnessed. This feature article covers some of the most intriguing total syntheses and synthetic studies towards the meroterpenoid class of natural products from the last five years.

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.

Total synthesis of the potent antifungal agents bengazole C and E

2009 ◽  
Vol 74 (6) ◽  
pp. 887-900 ◽  
Author(s):  
Álvaro Enríquez-García ◽  
Steven V. Ley
Keyword(s):  
Natural Products ◽  
Antifungal Activity ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Antifungal Agents ◽  
Nitrile Oxide ◽  
Total Syntheses ◽  
Unique Structure

The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds

2018 ◽  
Vol 47 (21) ◽  
pp. 8030-8056 ◽  
Author(s):  
Hiroshi Takikawa ◽  
Arata Nishii ◽  
Takahiro Sakai ◽  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Polycyclic Compounds ◽  
Total Syntheses ◽  
Naturally Occurring

This review has outlined the strategies and tactics of using arynes in the total syntheses of polycyclic natural products.

scholarly journals Contiguous Quaternary Carbons: A Selection of Total Syntheses

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3841
Author(s):  
Alina Eggert ◽  
Christoph Etling ◽  
Dennis Lübken ◽  
Marius Saxarra ◽  
Markus Kalesse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Status Quo ◽  
Total Syntheses ◽  
The Status ◽  
Selection Of ◽  
Quaternary Carbons

Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons.

Construction of sulfur-containing moieties in the total synthesis of natural products

2020 ◽  
Vol 37 (2) ◽  
pp. 246-275 ◽  
Author(s):  
Nengzhong Wang ◽  
Puli Saidhareddy ◽  
Xuefeng Jiang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Total Syntheses ◽  
Sulfur Containing

This review surveys the total syntheses of sulfur-containing natural products where sulfur atoms are introduced with different sulfurization agents to construct related sulfur-containing moieties.

Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products

2019 ◽  
Vol 36 (11) ◽  
pp. 1589-1605 ◽  
Author(s):  
Chao Zheng ◽  
Shu-Li You
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Indole Derivatives ◽  
Total Syntheses ◽  
Catalytic Asymmetric

The recent enantioselective total syntheses of natural products enabled by catalytic asymmetric dearomatization reactions of indole derivatives are presented.

scholarly journals A Reliable Enantioselective Route to Mono-Protected N1-Cbz Piperazic Acid Building Block

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5939
Author(s):  
Evanthia Papadaki ◽  
Dimitris Georgiadis ◽  
Michail Tsakos
Keyword(s):  
Natural Products ◽  
Amino Acid ◽  
Total Synthesis ◽  
Building Block ◽  
Optical Purity ◽  
Protecting Group ◽  
High Optical Purity

The chiral N1-Cbz, N2-H derivative of the piperazic acid monomer is a valuable building block in the total synthesis of natural products, comprising this nonproteinogenic amino acid. In that context, we wish to report an improved synthetic protocol for the synthesis of both (3R)- and (3S)-piperazic acids bearing the carboxybenzyl protecting group (Cbz) selectively at the N1 position. Our method builds on previously reported protocols, circumventing their potential shortcomings, and optimizing the ultimate selective deprotection at the N2 position, thus, offering an efficient and reproducible pathway to suitably modified piperazates in high optical purity.

scholarly journals Total synthesis of the azolemycins

2016 ◽  
Vol 14 (4) ◽  
pp. 1450-1454 ◽  
Author(s):  
Zoe J. Anderson ◽  
David J. Fox
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Analogue ◽  
Total Syntheses

The first total syntheses of newly isolated polyazole natural products azolemycins A–D, along with the synthesis of the tetra-oxazole non-natural analogue, are described.

scholarly journals Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1199
Author(s):  
Sijia Chen ◽  
Chongguo Jiang ◽  
Nan Zheng ◽  
Zhen Yang ◽  
Lili Shi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
Total Syntheses

Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be discussed. Focusing on the panorama of organic synthesis, this review highlights the strategically developed Pauson-Khand reaction in fulfilling total synthetic tasks and its synthetic attractiveness is aimed to be illustrated.

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