Concise review on isolation, biological activity, structure elucidation, and total synthetic approaches of 16-membered C2-symmetric macrolide pyrenophorol

Concise review on isolation, biological activity, structure elucidation, and total synthetic approaches of 16-membered C2-symmetric macrolide pyrenophorol

This review article provided isolation, biological activity, structural elucidation, and summary of the comprehensive synthesis of the sixteen-membered C2-symmetric macrolide dilactone pyrenophorol. Pyrenophorol has powerful antifungal activity against both Microbotryum violaceum and Saccharomyces c...

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Bibliographic Details
Published in:Synthetic communications Vol. 54; no. 5; pp. 323 - 347
Main Authors: Anusha, Bheemreddy, Kothapalli, Raveendra Babu, Victor Prem Sagar, Miriyala, Surendra, Bairla, Subba Reddy, Ummareddy Venkata
Format: Journal Article
Language:English
Published: Philadelphia Taylor & Francis 03-03-2024
Taylor & Francis Ltd
Subjects:
Asymmetry
Biological activity
Cascade chemical reactions
Chemical reactions
E coli
Epoxidation
Esterification
Fungicides
Grignard reactions
Hydroxylation
isolation
Ketones
Metathesis
Natural products
Oxidation
Pyrenophorol
stereochemistry
structural elucidation
Synthesis
total synthesis
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Summary:This review article provided isolation, biological activity, structural elucidation, and summary of the comprehensive synthesis of the sixteen-membered C2-symmetric macrolide dilactone pyrenophorol. Pyrenophorol has powerful antifungal activity against both Microbotryum violaceum and Saccharomyces cerevisiae, as well as potent antimicrobial activity against Microbotryum violaceum, Chlorella fusca, Escherichia coli, and Bacillus megaterium. It possesses selective phytotoxicity toward wild oats as well as notable anthelmintic properties. Due to the prominent biological activity of this natural product and its attractive C2-symmetric structure, numerous research groups have been attracted and reported the total synthesis of this natural product via vital organic reactions such as photo-induced rearrangement of an α-epoxy diazomethyl ketone to 4-hydroxy-2-alkenoate, intramolecular Wittig reaction, Sharpless asymmetric epoxidation, Grubb’s cross metathesis, reductive elimination of iodoepoxide, Rh-catalysed Asymmetric Hydro-Formylation (AHF) tandem reaction, the Novozym 435-catalyzed acrylation, hydrolytic kinetic resolution, Grignard reaction, Swern oxidation, CBS reduction, Pinnick oxidation, Photo Induced rearrangement, Yamaguchi esterification, Baeyer-Villager oxidation, McMillan asymmetric hydroxylation, Horner–Wadsworth–Emmons olefination and Mitsunobu cyclization.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2023.2297966