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

• 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
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2023.2297966

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.