Metal-catalyzed, bidentate directing group-assisted C−H functionalization: Application to the synthesis of complex natural products

Reddy, Motatipally Damoder; Dilipkumar, Uredi; Watkins, E. Blake

doi:10.1016/b978-0-12-817901-7.00004-6

Bioactive Natural Products

2019

DOI: 10.1016/b978-0-12-817901-7.00004-6

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Metal-catalyzed, bidentate directing group-assisted C−H functionalization: Application to the synthesis of complex natural products

Motatipally Damoder Reddy

Uredi Dilipkumar

E. Blake Watkins

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Cited by 8 publications

References 142 publications

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Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Dalal,

Babu,

Banga

2023

Asian J Org Chem

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A wide range of polyaryl compounds (π‐extended biaryls) including terphenyls, tetraphenyls, pentaphenyls, and hexaphenyls were assembled in a single operation of Pd(II)‐catalyzed C−H coupling of biaryl carboxamides and iodobiaryls. Traditionally, cross‐coupling protocols involving organometallic reagents were employed to assemble the core structure of π‐extended biaryls (polyphenylenes or polyaryls). The pre‐assembling of organometallic reagents is a limitation in investigations pertaining to the aryl‐aryl cross‐coupling reactions affording polyaryls (polyphenylenes). We report the application of Pd(II)‐catalyzed bidentate directing group (DG)‐aided C−H arylation method for constructing polyaryl motifs (π‐extended biaryls) using biaryl‐based carboxamides and iodobiaryls as the coupling partners in a single operation. The current investigation on the bidentate DG‐aided C−H arylation of biaryl carboxamides with iodobiaryls is expected to serve as a useful route to enrich the library of π‐extended biaryls (polyphenylenes or polyaryls).

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Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Dalal,

Babu,

Banga

2023

Asian J Org Chem

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Construction of C5‐Indole Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed β‐C(sp³)‐H Functionalization

Patel,

Babu,

Tomar

2024

Eur J Org Chem

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We report the construction of C5‐indole unnatural amino acid derivatives via the diastereoselective Pd(II)‐catalyzed prochiral β‐C(sp3)‐H arylation of racemic (DL), and enantiopure L‐ and D‐carboxamides of amino acids with 5‐iodoindoles. Independently, indole‐based compounds and amino acid motifs are important small molecules in organic synthesis and drug discovery research. This report aimed to contribute to enriching the library of indole‐based unnatural amino acid derivatives. The synthesis of examples of C5‐indole motif‐installed amino acid derivatives comprising norvaline, phenylalanine, leucine, norleucine, 2‐aminooctanoic acid having anti‐stereochemistry was accomplished. The synthesis of the C5‐indole motif‐containing non‐α‐amino acid (aminoalkanoic acid) derivatives was also reported. The C‐H arylation reactions of racemic and enantiopure carboxamides with 5‐iodoindoles afforded the corresponding indole unnatural amino acid derivatives with good diastereoselectivity (anti, dr >95:5 and enantiopurity (er up to 99:1). Removal of the directing group (8‐aminoquinoline), phthalimide group and preparation of indole amino acid esters and free amino group‐containing indole unnatural amino acid motifs were also shown. The utility of the methodology was shown by synthesizing indole motif‐containing pyrrolidone and peptide molecules. The stereochemistry of the major (anti) diastereomers was ascertained from the X‐ray structure of a representative compound.

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Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp³C−H Functionalization

Banga,

Babu

2024

Eur J Org Chem

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This paper reports the construction of racemic and enantiopure (D‐ and L‐) fluorene and fluorenone‐based novel unnatural amino acid derivatives. The Pd(II)‐catalyzed bidentate directing group‐aided arylation of prochiral β‐C(sp3)‐H bonds in racemic, enantiopure carboxamides of amino acids with iodofluorenes was reported. The construction of novel examples of fluorene and fluorenone motifs containing amino acids comprising of norvaline, leucine, phenylalanine, norleucine, 2‐aminooctanoic acid derivatives having the anti‐stereochemistry (with good enantiopurity) was accomplished. The construction of bis fluorenyl alanine scaffolds and fluorenyl motif‐containing non‐α‐amino acid (aminoalkanoic acid) derivatives was also reported. Examples of removal of the directing group (8‐aminoquinoline) and phthalimide‐protecting group present in the fluorenyl‐based unnatural amino acid derivatives have been shown. Accordingly, fluorene motif‐based amino acid esters and free amino group‐containing unnatural amino acid derivatives were synthesized. The stereochemistry of the major (anti) diastereomers obtained via the prochiral β‐C(sp3)‐H arylation of norvaline, leucine, phenylalanine, norleucine, 2‐aminooctanoic acid derivatives was ascertained from the X‐ray structure of a representative compound. Fluorene‐ and fluorenone‐based motifs are vital skeletons in materials and medicinal chemistry research. Accordingly, this work is a contribution towards enriching the library of fluorene and fluorenone unnatural amino acid scaffolds.

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Metal-catalyzed, bidentate directing group-assisted C−H functionalization: Application to the synthesis of complex natural products

Cited by 8 publications

References 142 publications

Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Construction of C5‐Indole Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed β‐C(sp³)‐H Functionalization

Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp³C−H Functionalization

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Metal-catalyzed, bidentate directing group-assisted C−H functionalization: Application to the synthesis of complex natural products

Cited by 8 publications

References 142 publications

Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls

Construction of C5‐Indole Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed β‐C(sp3)‐H Functionalization

Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp3C−H Functionalization

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Construction of C5‐Indole Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed β‐C(sp³)‐H Functionalization

Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp³C−H Functionalization