Total Synthesis of Anticancer Pacharin, Bauhiniastatin 4, and Bauhinoxepins C and D

Pattarapon Sang-aroon; Norasian Boosaman; Intouch Rakchaya; Wiradet Siri; Asamaporn Tieojaroenkit; Nutthawat Chuanopparat; Paiboon Ngernmeesri

doi:10.1055/a-2550-7239

Synthesis, Table of Contents

Synthesis 2025; 57(12): 1941-1954
DOI: 10.1055/a-2550-7239

paper

Total Synthesis of Anticancer Pacharin, Bauhiniastatin 4, and Bauhinoxepins C and D

Authors

Pattarapon Sang-aroon‡

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Norasian Boosaman‡

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Intouch Rakchaya‡

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Wiradet Siri

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Asamaporn Tieojaroenkit

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Nutthawat Chuanopparat

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Paiboon Ngernmeesri ∗

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

Abstract

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Abstract

Reported herein is the total synthesis of anticancer pacharin, bauhiniastatin 4, and bauhinoxepins C and D. The synthetic strategy features a cascade reaction involving intermolecular nucleophilic aromatic substitution followed by intramolecular Knoevenagel condensation to form a dibenzo[b,f]oxepine scaffold of these compounds. Pacharin and bauhiniastatin 4 were synthesized in eight steps from 2-methylresorcinol with overall yields of 5.4% and 8.3%, respectively. Similarly, bauhinoxepins C and D were synthesized in seven steps with overall yields of 3.5% and 2.6%, respectively. This methodology offers an efficient route for accessing these natural products with implications for medicinal and synthetic chemistry.

Key words

natural product synthesis - cascade reaction - dibenzo[b,f]oxepines - anticancer agents - nucleophilic aromatic substitution - Knoevenagel condensation

Full Text

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Supplementary Material

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