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 Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review

2018 ◽  
Vol 15 (1) ◽  
pp. 3-20 ◽  
Author(s):  
Vahideh Zadsirjan ◽  
Majid M. Heravi
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Conjugate Addition ◽  
Chiral Auxiliary ◽  
Addition Reactions ◽  
Chiral Auxiliaries ◽  
Complex Molecules ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Wide Range

Background: The most frequently used chiral auxiliaries, oxazolidinones (Evans' oxazolidinones) have been employed in 1,4-congugate addition reactions to α,β-unsaturated carbonyl compounds. Supplementary to our previous reports in this mini-review, we attempted to underscore the applications of this strategy in a step (steps) in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Objective: In this mini-review, we try to underscore the applications of oxazolidinones (Evans’ oxazolidinones) in 1,4-congugate addition reactions to α,β-unsaturated carbonyl in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Conclusion: In spite of well-known superiority of asymmetric catalyzed reactions, the use of auxiliarycontrolled reactions are still considered as commanding, vital and sometimes as only tools in the generation of stereogenic centers during the construction of complex molecules and total synthesis of naturally occurring compounds. The commercial availability, or readily accessibility of a wide variety of chiral amino alcohols as starting materials to synthesize a wide range of oxazolidinones is the merits of them. In addition, the ease of removal and subjection to various and diverse stereoselective reactions make oxazolidinones as the ideal and superior chiral auxiliaries. In this regard, they were successfully used in asymmetric 1,4-conjugate addition reactions with high stereoselectivities. The high degree of asymmetric induction can be attributed to the rigid chelation of N-acyloxazolidinones with metal ions, as well as the covering of one face of the system by the bulkiness of 4-substituent. In summary, in this report, the importance of the applications of chiral oxazolidinones as suitable chiral auxiliaries in the stereoselective, 1,4-conjugate addition reactions in asymmetric synthesis and in particular, the total synthesis of naturally occurring compounds and some complex molecules were underscored. Noticeably, in these total syntheses, this chiral auxiliary is controlling the stereochemistry of a newly created stereogenic center as well as preserving the configuration of other chiral centers, which already have been presented in the precursor. General methods have been established for the attachment of the chiral auxiliary as a moiety to the substrate molecule in high to excellent yields. At the end of these reactions, this auxiliary can be easily removed leaving various desired reactive motifs for the next step in multi-step synthesis.

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.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

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.

Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction

2020 ◽  
Vol 18 (12) ◽  
pp. 2331-2345
Author(s):  
Joy Chakraborty ◽  
Ankan Ghosh ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Total Syntheses ◽  
Naturally Occurring

Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article.

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 Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (–)-Atrop-abyssomicin C

2017 ◽  
Vol 12 (8) ◽  
pp. 1934578X1701200
Author(s):  
Filip Bihelovic ◽  
Bojan Vulovic ◽  
Radomir N. Saicic
Keyword(s):  
Natural Products ◽  
Synthetic Route ◽  
Synthetic Methodology ◽  
General Applicability ◽  
Total Syntheses ◽  
New Methods ◽  
Naturally Occurring

During our attempt to follow the planned synthetic route to the naturally occurring antibiotic (–)- atrop-abyssomicin C, we encountered two shortcomings, which forced us to reconsider our tactics and find new methods to overcome the problems. These methods turned out to be of general applicability, as demonstrated later in total syntheses of two other natural products: (+)-allokainic acid and (-)-gabosine H. The paper provides a brief account of these endeavors.

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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