Use of furans in synthesis of bioactive compounds

Lee, Hing Ken; Chan, Kin‐Fai; Hui, Chi Wai; Yim, Ho Kee; Wu, Xun; Wong, H. N. C.

doi:10.1351/pac200577010139

Cited by 98 publications

(21 citation statements)

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“…Multisubstituted furans are of importance because numerous compounds bearing such a heterocyclic ring exhibit a wide range of biological activities and are also building blocks for organic synthesis 29,30. The development of new and efficient syntheses of multisubstituted furans having specific substitution patterns is an important objective 31…”

Section: Resultsmentioning

confidence: 99%

Mutually Complementary Metal‐ and Organocatalysis with Collective Synthesis: Asymmetric Conjugate Addition of 1,3‐Carbonyl Compounds to Nitroenynes and Further Reactions of the Products

Peng

et al. 2012

Adv Synth Catal

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The first metal-catalyzed 1,4-selective asymmetric addition of malonates to nitroenynes promoted by a simple chiral nickel(II)-diamine catalyst, was developed, facilitating a mild synthesis of a novel type of multifunctional chiral b-alkynyl acids bearing a nitro group. Based on this protocol, we have developed a practical and collective synthesis of a series of diverse functional molecules and building blocks including new types of chiral balkynyl-g-amino acids, b-functionalized chiral dketo-g-lactones, chiral g-alkylidenelactones, alkynylsubstituted pyrrole-3-carboxylic acid derivatives, tetrasubstituted furans and chiral b-alkynyl-g-lactams. Notably, we discovered two unusual tandem reactions leading to functionalized chiral 1,5-dicarbonyl compounds. In addition, by employing simple bifunctional organocatalysts, we have developed the first regio-, diastereo-and enantioselective conjugate addition of a-substituted b-keto esters to nitroenynes, which is poorly diastereoselective with chiral nickel(II)-diamine catalysts, providing a new entry to adjacent quaternary and tertiary stereocenters in one step. Based on this protocol, we have developed a concise asymmetric synthesis of conformationally constrained bicyclic g 2 -amino acids featuring an alkynyl side chain with an adjacent quaternary carbon stereocenter. The study described here demonstrates that the mutually complementary strategy of transition metal catalysis and organo-catalysis is a powerful and promising tool in catalytic asymmetric synthesis.

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Section: Resultsmentioning

confidence: 99%

Mutually Complementary Metal‐ and Organocatalysis with Collective Synthesis: Asymmetric Conjugate Addition of 1,3‐Carbonyl Compounds to Nitroenynes and Further Reactions of the Products

Peng

et al. 2012

Adv Synth Catal

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“…Over the past decade, a few impressive strategies in the area of racemic 3,4‐fused bicyclic furans synthesis have been reported . During the same time, our group has developed a series of the metal‐catalyzed intermolecular cycloaddition of 2‐(1‐alkynyl)‐2‐alken‐1‐ones with imines, [4a] 3‐styrylindoles, [4b] 1,3‐diphenyl‐isobenzofuran, [4c] and nitrones, [4d] which have been extensively used for the synthesis of racemic 3,4‐fused bicyclic furans derivatives .…”

Section: Background and Originality Contentmentioning

confidence: 99%

Ming‐Phos/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐d][1,2]oxazines^†

Zhou

et al. 2020

Chin. J. Chem.

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of main observation and conclusion A gold(I)-catalyzed asymmetric intermolecular tandem [3+3]-cyclization reaction of 2-(1-alkynyl)-2alken-1-ones with nitrones has been developed by using Ming-Phos as a chiral ligand. This method enables access to the stereodivergent synthesis of highly substituted furo[3,4-d][1,2]oxazines in excellent efficiency and stereoselectivity (up to 99% yield, 99% ee, >20 : 1 dr). Scheme 1 Previous results and this work on asymmetric [3+3] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with nitrones 578 www.cjc.wiley-vch.de

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“…Moreover, a furan heterocycle itself is of significant interest as a synthon towards an array of valuable intermediates [66][67][68][69][70][71][72][73]. Thus, it is not surprising that the development of selective and general methods for the facile assembly of the furan core has attracted tremendous interest over the past decades [74][75][76][77][78][79].…”

Section: Furansmentioning

confidence: 99%

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

Dudnik

Gevorgyan

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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Aromatic heterocycles, particularly furans and pyrroles, are structural motifs found in a vast number of biologically active natural and artificial compounds [1][2][3]. Other examples of practical applications of furans and pyrroles include dyes, polymers, and electronic materials [4]. Moreover, these heterocycles are employed as important intermediates in organic synthesis [5][6][7][8][9]. The successful application of furans and pyrroles in these and many other ways and their significance in applied and fundamental areas have placed them at the forefront of contemporary organic chemistry. A variety of methodologies and different protocols for their synthesis have been reported [1-3, 10-23] and become well established throughout decades. Among the variety of novel approaches for the synthesis of furans and pyrroles, transition metal-catalyzed transformations are arguably the most attractive methodologies . Several excellent reviews on the transition metal-catalyzed synthesis of monocyclic five-membered heterocycles have been published in the literature. Many of them were categorized by either the metal or the type of transformation. This chapter covers transition metal-catalyzed syntheses of furans and pyrroles. The main organization of this chapter is based on a heterocycle, wherein syntheses of a particular core are structured by the type of transformation and substrates engaged. Herein, we have tried to discuss equally the synthetic applicability of a method and mechanistic aspects and concepts implicated in the described transformations. A discussion of the mechanisms is given when needed to provide an idea about possible reaction pathways and the nature of the elementary processes involved in the catalytic transformation. It should be noted that the most essential and general catalytic reactions, as well as recent and conceptionally interesting transformations, are discussed in more detail in this chapter. Syntheses of furans and pyrroles via functionalization of the preexisting heterocyclic cores [37,[52][53][54][55][56][57][58][59][60] are not covered and, therefore, only reactions in which assembly of a heterocyclic ring occurs are described. In addition, the Pd-catalyzed synthesis of heterocycles is not covered herein, as this topic is covered in Chapter 6.

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Use of furans in synthesis of bioactive compounds

Abstract: Synthetic approaches to the total synthesis of plakortone B, as well as diastereoselective nucleophilic additions to furyl aldehyde and furyl sulfonylimine employing chiral 3-boronates as auxiliary are presented.

Cited by 98 publications

References 5 publications

Mutually Complementary Metal‐ and Organocatalysis with Collective Synthesis: Asymmetric Conjugate Addition of 1,3‐Carbonyl Compounds to Nitroenynes and Further Reactions of the Products

Mutually Complementary Metal‐ and Organocatalysis with Collective Synthesis: Asymmetric Conjugate Addition of 1,3‐Carbonyl Compounds to Nitroenynes and Further Reactions of the Products

Ming‐Phos/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐d][1,2]oxazines^†

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

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Use of furans in synthesis of bioactive compounds

Abstract: Synthetic approaches to the total synthesis of plakortone B, as well as diastereoselective nucleophilic additions to furyl aldehyde and furyl sulfonylimine employing chiral 3-boronates as auxiliary are presented.

Cited by 98 publications

References 5 publications

Mutually Complementary Metal‐ and Organocatalysis with Collective Synthesis: Asymmetric Conjugate Addition of 1,3‐Carbonyl Compounds to Nitroenynes and Further Reactions of the Products

Mutually Complementary Metal‐ and Organocatalysis with Collective Synthesis: Asymmetric Conjugate Addition of 1,3‐Carbonyl Compounds to Nitroenynes and Further Reactions of the Products

Ming‐Phos/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐d][1,2]oxazines†

Transition Metal‐Catalyzed Synthesis of Monocyclic Five‐Membered Aromatic Heterocycles

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Ming‐Phos/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐d][1,2]oxazines^†