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.

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.

scholarly journals Directed aromatic functionalization in natural-product synthesis: Fredericamycin A, nothapodytine B, and topopyrones B and D

2011 ◽  
Vol 7 ◽  
pp. 1475-1485 ◽  
Author(s):  
Charles Dylan Turner ◽  
Marco A Ciufolini
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Fredericamycin A

This is a review of our efforts toward the synthesis of a group of natural products that display noteworthy biological activity: Fredericamycin A, nothapodytine B, and topopyrones B and D. In each case, directed aromatic functionalization methodology greatly facilitated the assembly of the key molecular subunits.

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.

Construction of piperidine-2,4-dione-type azaheterocycles and their application in modern drug development and natural product synthesis

2020 ◽  
Vol 18 (15) ◽  
pp. 2793-2812 ◽  
Author(s):  
Rabdan M. Tikhov ◽  
Nikolai Yu. Kuznetsov
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Drug Development ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Modern Drug

The review surveys the existing routes to piperidine-2,4-dione-type heterocycles including derivatives with the most vital types of biological activity. This heterocyclic platform is ideal for the construction of modern drugs and natural products.

A Decade with Dötz Benzannulation in the Synthesis of Natural Products

Synlett ◽  
2020 ◽  
Vol 31 (05) ◽  
pp. 403-420 ◽  
Author(s):  
Rodney A. Fernandes ◽  
Anupama Kumari ◽  
Ramdas S. Pathare
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
General Description ◽  
The Past ◽  
Rapid Construction ◽  
Molecular Architectures

The Dötz benzannulation is a named reaction that utilizes Fischer chromium carbenes in a formal [3+2+1] cycloaddition with an alkyne and CO to produce the corresponding benzannulated product. Since its development in the 1970s, this reaction has been extensively used in the synthesis of natural products and various molecular architectures. Although the reaction sometimes suffers from the formation of other competing side products, the rapid construction of naphthol structures with a 1,4-dihydroxy unit makes it the most appropriate reaction for the synthesis of p-naphthoquinones. This review focuses on our group’s efforts over the past decade on the extensive use of this annulation reaction along with the contributions of others on the synthesis of different natural products.1 Introduction2 General Description and Mechanism of the Dötz Benzannulation Reaction3 Applications of the Dötz Benzannulation in Natural Product Synthesis over the Last Decade4 Conclusion

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.

Stereoconfining macrocyclizations in the total synthesis of natural products

2019 ◽  
Vol 36 (11) ◽  
pp. 1546-1575 ◽  
Author(s):  
Kuan Zheng ◽  
Ran Hong
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
The Past

This review covers selected examples of point chirality-forming macrocyclizations in natural product total synthesis in the past three decades.

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