Total Synthesis and Biological Evaluation of Seiricuprolide and Pestalotioprolide B
Issued Date
2023-04-03
Resource Type
ISSN
1434193X
eISSN
10990690
Scopus ID
2-s2.0-85149044105
Journal Title
European Journal of Organic Chemistry
Volume
26
Issue
13
Rights Holder(s)
SCOPUS
Bibliographic Citation
European Journal of Organic Chemistry Vol.26 No.13 (2023)
Suggested Citation
Sanphetchaloemchok P., Saikachain N., Khumjiang R., Muanprasat C., Tadpetch K. Total Synthesis and Biological Evaluation of Seiricuprolide and Pestalotioprolide B. European Journal of Organic Chemistry Vol.26 No.13 (2023). doi:10.1002/ejoc.202300034 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/81741
Title
Total Synthesis and Biological Evaluation of Seiricuprolide and Pestalotioprolide B
Author's Affiliation
Other Contributor(s)
Abstract
The first total syntheses of seiricuprolide and pestalotioprolide B, rare 14-membered α,β-unsaturated macrolides embedding a chiral epoxide motif, were achieved in 17 steps with 1.9 % and 1.6 % overall yields, respectively. Our synthesis featured the key Shiina macrolactonization to construct the 14-membered macrocyclic skeleton, Wittig olefination to generate the (E)-α,β-unsaturated ester and selective reduction of advanced chiral propargylic alcohol intermediate to enable the exclusive formation of Z- or E-olefin at C8−C9. Synthetic seiricuprolide and pestalotioprolide B were evaluated for their cytotoxic activity against the HCT116 colon cancer cell line as well as their inhibitory effect on CFTR chloride channel activity in human intestinal epithelial (T84) cells. Preliminary structure–activity relationship suggested that the C5−C6 β-epoxide moiety suppressed both biological activities.