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https://open.uns.ac.rs/handle/123456789/30879
Title: | Divergent total synthesis of crassalactones B and C and evaluation of their antiproliferative activity | Authors: | Benedeković Goran Kovačević Ivana Popsavin Mirjana Francuz Jovana Kojić Vesna Bogdanović Gordana Popsavin Velimir |
Issue Date: | 2015 | Journal: | Tetrahedron | Abstract: | © 2015 Elsevier Ltd. All rights reserved. A divergent total synthesis of cytotoxic natural products (+)-crassalactones B (2) and C (3) has been achieved by utilizing diacetone d-glucose (4) as a chiral precursor. The key steps of the synthesis of both targets 2 and 3 were a stereo-selective addition of phenyl magnesium bromide to a dialdose derivative, a regioselective introduction of the cinnamic acid residue, and a stereospecific furano-lactone ring formation by cyclocondensation of a suitable hemiacetal derivative with Meldrum's acid. No protection is necessary for the synthesis of the (+)-crassalactone C (3), except the diacetonide function that is already present in the commercially available starting material 4. Preparation of (+)-crassalactone B (2) from the same starting material, requires the use of a single silyl ether protecting group throughout the synthesis. The synthesized natural products were evaluated for their in vitro antiproliferative activity against PC3, HT29 and A549 human tumour cell lines. | URI: | https://open.uns.ac.rs/handle/123456789/30879 | ISSN: | 0040-4020 | DOI: | 10.1016/j.tet.2015.05.040 |
Appears in Collections: | PMF Publikacije/Publications |
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