Synonyms:discodermolide
98% *data from raw suppliers
DISCODERMOLIDE 95.00% *data from reagent suppliers
There total 30 articles about Discodermolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 95.0%
Reference yield: 87.0%
Reference yield: 85.0%
The study presents a novel protocol for the stereoselective synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide, a potent anti-cancer agent, through diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones. Key chemicals used include R-pinene-based chiral "allyl"-borane reagents for introducing initial chirality, Grubbs's second-generation ruthenium catalyst for ring-closing metathesis reactions, OsO4/NMO for dihydroxylation, phenylchlorothionoformate and tributyltin hydride for regioselective deoxygenation, and various protecting groups and reagents for functional group transformations. These chemicals served the purpose of constructing the complex molecular structures of the subunits with high stereochemical control, which is crucial for their potential application in cancer treatment therapies.
The research aims to develop a practical and scalable total synthesis of (+)-discodermolide, a microtubule-stabilizing anticancer agent, by relying solely on substrate-based stereocontrol. The study employs a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2, using 1,3-diol 7 as a common building block for the C1?C5, C9?C16, and C17?C24 subunits. Key chemicals used include (Z)-enone 3, aldehyde 2, 1,3-diol 7, and Roche ester (S)-8. The researchers successfully synthesized (+)-discodermolide through a highly convergent and practical route, achieving a yield of 5.1% over 24 linear steps. The synthesis relies on substrate control to configure all stereocenters and exploits remote 1,6-asymmetric induction in boron-mediated aldol reactions. The study concludes that this new route is applicable for preparing multigram quantities of (+)-discodermolide, facilitating further biological and clinical studies, and providing access to novel analogues for structure-activity relationship (SAR) studies.
The research describes the total synthesis of a potent hybrid of the anticancer natural products dictyostatin and discodermolide. The hybrid was designed to have enhanced cell growth inhibitory activity compared to discodermolide, and it was found to retain this potent activity even against the Taxol-resistant NCI/ADR-Res cell line. The synthesis involved a series of chemical reactions, including a cross-coupling–macrolactonisation endgame, a Still–Gennari ole?nation, and a copper-mediated Stille cross-coupling. Key chemicals used in the synthesis include aldehyde 47, b-ketophosphonate 5, lactate-derived ketone 79, aldehyde 8, vinyl iodide 14, stannane 6, and various reagents for reduction, hydrolysis, and protection steps. The resulting hybrid 3 demonstrated low nanomolar cell growth inhibitory activity in vitro against four human cancer cell lines, suggesting its potential as a novel anticancer agent. The study also explored the contribution of the C7,C9-diol to the pharmacophore by synthesizing and testing an acetonide derivative 15, which had significantly reduced cytotoxicity.
What can I do for you?
Get Best Price
Total 8 Pictures about this product
