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

The multistep synthesis of natural products has historically served as a useful and informative platform for showcasing the best, state-of-the-art synthetic methodologies and technologies. Over the last several decades, electrochemistry has proved itself to be a useful tool for conducting redox reactions. This is primarily due to its unique ability to selectively apply any oxidizing or reducing potential to a sufficiently conductive reaction solution. Electrochemical redox reactions are readily scaled and can be more sustainable than competing strategies based on conventional redox reagents. In this chapter, we summarize the examples where electrochemistry has been used in the synthesis of natural products. The chapter is organized by the reaction type of the electrochemical step and covers both oxidative and reductive reaction modes.

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Recent results toward the stereoselective synthesis of biologically active natural products

Pure and Applied Chemistry ◽

10.1351/pac200779020163 ◽

2007 ◽

Vol 79 (2) ◽

pp. 163-172 ◽

Cited By ~ 2

Author(s):

Luiz C. Dias ◽

Luciana G. de Oliveira ◽

Paulo R. R. Meira

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Cell Cultures ◽

Stereoselective Synthesis ◽

Animal Cell ◽

Biologically Active ◽

Asymmetric Total Synthesis ◽

Callystatin A ◽

Animal Cell Cultures ◽

Active Natural

This paper describes the convergent and stereocontrolled asymmetric total synthesis of (+)-crocacins C and D, potent inhibitors of animal cell cultures and several yeasts and fungi, and (-)-callystatin A, a potent antitumor polyketide.

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ChemInform Abstract: Total Synthesis of Biologically Active Natural Products Possessing Unique Structural Features

ChemInform ◽

10.1002/chin.200008311 ◽

2010 ◽

Vol 31 (8) ◽

pp. no-no

Author(s):

Tadashi Katoh

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Structural Features ◽

Biologically Active ◽

Active Natural

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Total Synthesis of Biologically Active Natural Products Possessing Unique Structural Features.

Journal of Synthetic Organic Chemistry Japan ◽

10.5059/yukigoseikyokaishi.57.736 ◽

1999 ◽

Vol 57 (9) ◽

pp. 736-748 ◽

Cited By ~ 3

Author(s):

Tadashi KATOH

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Structural Features ◽

Biologically Active ◽

Active Natural

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Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions

Synlett ◽

10.1055/s-0037-1610126 ◽

2018 ◽

Vol 29 (12) ◽

pp. 1552-1571 ◽

Cited By ~ 11

Author(s):

Jianxian Gong ◽

Zhen Yang ◽

Yueqing Gu ◽

Ceheng Tan

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Cascade Reactions ◽

Cascade Reaction ◽

Biologically Active ◽

Synthetic Methods ◽

Left Wing ◽

Asymmetric Total Synthesis ◽

Diversity Oriented Synthesis ◽

Active Natural

This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.1 Introduction2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids2.2 Synthesis of Left-Wing Fragment of Azadirachtin I2.3 Collective Synthesis of Cladiellins3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins3.2 Total Synthesis of Orientalol F3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C4 Summary and Outlook

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