Recent Advances on the Application of Electrocyclic Reactions in Complex Natural Product Synthesis

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4383-4413 ◽  
Author(s):  
Ming Bian ◽  
Hanfeng Ding ◽  
Lekai Li
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Electrocyclic Reactions ◽  
Recent Advances ◽  
Electrocyclic Reaction

The electrocyclic reaction is one of the most powerful tools for the construction of complex polycyclic scaffolds in a highly stereocontrolled fashion. In this review, recent advances in its application in the total synthesis of representative natural products are discussed, with the aim of providing a complement to existing reviews.1 Introduction2 4π Electrocyclization2.1 Neutral 4π Electrocyclization2.2 Cationic 4π Electrocyclization3 6π Electrocyclization3.1 All-Carbon 6π Electrocyclization3.2 Oxa-6π Electrocyclization3.3 Aza-6π Electrocyclization3.4 Retro-6π Electrocyclization4 8π Electrocyclization5 Conclusion and Outlook

scholarly journals Recent advances in the total synthesis of cyclobutane-containing natural products

2020 ◽  
Vol 7 (1) ◽  
pp. 136-154 ◽  
Author(s):  
Jinshan Li ◽  
Kai Gao ◽  
Ming Bian ◽  
Hanfeng Ding
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Recent Advances ◽  
Recent Developments

Recent developments of strategies on the construction of cyclobutanes and their application in complex natural product synthesis are discussed.

Recent advances in the synthesis of oxaspirolactones and their application in the total synthesis of related natural products

2019 ◽  
Vol 17 (31) ◽  
pp. 7270-7292 ◽  
Author(s):  
Sagar S. Thorat ◽  
Ravindar Kontham
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Medicinal Chemistry ◽  
Natural Product Chemistry ◽  
Structural Motifs ◽  
Recent Advances ◽  
Synthetic Molecules ◽  
Product Chemistry

Oxaspirolactones are ubiquitous structural motifs found in natural products and synthetic molecules with a diverse biochemical and physicochemical profile, and represent a valuable target in natural product chemistry and medicinal chemistry.

Ir-Catalyzed reactions in natural product synthesis

2018 ◽  
Vol 5 (1) ◽  
pp. 132-150 ◽  
Author(s):  
Pengquan Chen ◽  
Yuecheng Wu ◽  
Shifa Zhu ◽  
Huanfeng Jiang ◽  
Zhiqiang Ma
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Catalyzed Reactions

This review highlights the recent applications of Ir-catalyzed reactions in the total synthesis of natural products.

scholarly journals Recent Advance of Domino Michael Reaction in Natural Product Synthesis

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110498
Author(s):  
Hisahiro Hagiwara
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Michael Reaction ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Michael Reactions ◽  
Recent Advances ◽  
Key Steps ◽  
Related Compounds

Recent advances in the total syntheses of cyclic natural products and related compounds from 2005 to 2021, which employ domino Michael reactions as key steps, have been reviewed, focusing mainly on the domino Michael reactions catalyzed by organocatalysts.

Synthesis of α-exo-Methylene-γ-butyrolactone: Recent Developments and Applications in Natural Product Synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Weilong Liu ◽  
Nicolas Winssinger
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Vast Array ◽  
The Past ◽  
New Approaches ◽  
Recent Developments

The α-exo-methylene-γ-butyrolactone moiety is present in a vast array of structurally diverse natural products and is often central to their biological activity. In this review, we summarize new approaches to α-exo-methylene-γ-butyrolactones developed over the past decade as well as their applications in total synthesis.

Recent Advances in Steroid Synthesis: A Tribute to Sir Derek Barton

2018 ◽  
Vol 71 (9) ◽  
pp. 627
Author(s):  
Kieran D. Jones ◽  
Scott G. Stewart
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Methyl Ether ◽  
Ring System ◽  
Natural Product Synthesis ◽  
Steroid Synthesis ◽  
Research Areas ◽  
Recent Advances

The synthesis of steroids and gaining an ultimate understanding of their reactivity was one of Sir Derek Barton’s most notable research areas. This highlight will focus on the construction of the steroid ring system from 2016 to 2018, and will include pathways that eventually led to natural product synthesis. For example, efficient syntheses of ent-pregnanolone sulfate and oestradiol methyl ether will be explained along with the total synthesis of cannogenol-3-O-α-l-rhamnoside.

scholarly journals Exploiting the Limits of Divergency Scaffolds in Natural Product Synthesis: The Case Study of Sesquiterpenoids

2021 ◽  
Author(s):  
Vera P. Demertzidou ◽  
Alexandros Zografos
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Rational Design ◽  
Natural Product Synthesis ◽  
Oxidation States

Divergent synthesis is a powerful but yet underdeveloped method to address the usual drawbacks of poor supply and confined diversity in the total synthesis of natural products. Herein, we describe the rational design behind the selection and the synthesis of a divergency scaffold for sesquiterpenoid lactones synthesis, as a case study, which provides access to a rich collection of carbocycles in different oxidation states within 8,12-sesquiterpenoids through simple, scalable transformations.

scholarly journals Rhodium(ii)-catalysed intramolecular C–H insertion α- to oxygen: reactivity, selectivity and applications to natural product synthesis

2015 ◽  
Vol 13 (23) ◽  
pp. 6419-6431 ◽  
Author(s):  
Fanny J. Lombard ◽  
Mark J. Coster
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Oxygen Reactivity

This review highlights reactivity and selectivity trends for the insertion of Rh(ii) carbenes into C–H bonds that are activated by α-oxygen substituents, and the application of this reaction to the total synthesis of some natural products.

Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 421-433 ◽  
Author(s):  
Ken-ichi Takao ◽  
Akihiro Ogura ◽  
Keisuke Yoshida ◽  
Siro Simizu
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Total Syntheses

In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.1 Introduction2 Total Synthesis of (+)-Pestalotiopsin A3 Total Synthesis of (+)-Cytosporolide A4 Total Synthesis of (+)-Vibsanin A5 Total Syntheses of (+)-Aquatolide and Related Humulanolides6 Conclusion

scholarly journals Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12626-12652 ◽  
Author(s):  
Amardeep Awasthi ◽  
Mandeep Singh ◽  
Garima Rathee ◽  
Ramesh Chandra
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Contextual Information ◽  
Natural Product Synthesis ◽  
Biologically Active ◽  
Synthetic Methodologies ◽  
Active Natural

We have provided contextual information on the chemistry of 3-substituted phthalides and their significance in natural product synthesis.

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