The first total synthesis and revision of absolute stereochemistry of natural cytotoxic lactone cleistanolate. Kesić, J., Kovačević, I., Popsavin, M., Benedeković, G., Rodić, M., Kojić, V., & Popsavin, V. Bioorganic Chemistry, Academic Press Inc., 2022.
The first total synthesis and revision of absolute stereochemistry of natural cytotoxic lactone cleistanolate [link]Paper  doi  abstract   bibtex   
Development of a synthetic route applicable to \sc d-ribose and \sc d-xylose enabled the synthesis of cleistanolate putative structure, its five stereoisomers, and led to revision and confirmation of absolute stereochemistry of the natural product. Key steps of the synthesis included zinc-mediated THF ring-opening and stereoselective dihydroxylation under the Upjohn conditions. The first total synthesis of cleistanolate was completed in eight steps starting from \sc d-xylose. The C-5 stereocenter of the natural product was assigned the correct (5ıt S)-stereochemistry. Cytotoxicity of natural product was briefly investigated.
@ARTICLE{Kesic2022,
author={Kesić, J. and Kovačević, I. and Popsavin, M. and Benedeković, G. and Rodić, M.V. and Kojić, V. and Popsavin, V.},
title={The first total synthesis and revision of absolute stereochemistry of natural cytotoxic lactone cleistanolate},
journal={Bioorganic Chemistry},
year={2022},
volume={128},
doi={10.1016/j.bioorg.2022.106073},
art_number={106073},
url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-85135509887&doi=10.1016%2fj.bioorg.2022.106073&partnerID=40&md5=b294f4f0c277de0e79bab1b7f2a0a309},
abstract={Development of a synthetic route applicable to {\sc d}-ribose and {\sc d}-xylose enabled the synthesis of cleistanolate putative structure, its five stereoisomers, and led to revision and confirmation of absolute stereochemistry of the natural product. Key steps of the synthesis included zinc-mediated THF ring-opening and stereoselective dihydroxylation under the Upjohn conditions. The first total synthesis of cleistanolate was completed in eight steps starting from {\sc d}-xylose. The C-5 stereocenter of the natural product was assigned the correct (5{\it S})-stereochemistry. Cytotoxicity of natural product was briefly investigated.},
author_keywords={Cleistanolate;  Cytotoxicity;  Natural products;  Structure revision;  Total synthesis},
publisher={Academic Press Inc.},
issn={00452068},
coden={BOCMB},
abbrev_source_title={Bioorg. Chem.},
document_type={Article},
source={Scopus},
}

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