Journal ArticleDOI
Total synthesis of dysidiolide
E. J. Corey and,Bryan E. Roberts +1 more
Reads0
Chats0
TLDR
The cdc25A protein phosphatase inhibitor dysidiolide has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product.Abstract:
The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product. Once the central portion of 1 was established, elaboration of the side chains was accomplished expediently via steps that included (1) vinyl cuprate displacement of an iodide to complete the C-1 side chain, (2) a highly diastereoselective oxazaborolidine-catalyzed (CBS) reduction to form carbinol 11, and (3) photochemical oxidation of 11 to generate the γ-hydroxybutenolide functionality of 1. Additionally, this synthesis proves the absolute stereochemistry of dysidiolide (1).read more
Citations
More filters
Journal ArticleDOI
Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo‐ and Stereoselective Hydrogenation of Ketones
Ryoji Noyori,Takeshi Ohkuma +1 more
TL;DR: The newly devised [RuCl(2)(phosphane)(2)(1,2-diamine)] complexes are excellent precatalysts for homogeneous hydrogenation of simple ketones which lack any functionality capable of interacting with the metal center.
Journal ArticleDOI
Asymmetrische Katalyse mit hinsichtlich Struktur und Funktion gezielt entworfenen Molekülen: die chemo‐ und stereoselektive Hydrierung von Ketonen
Ryoji Noyori,Takeshi Ohkuma +1 more
Journal ArticleDOI
Compound library development guided by protein structure similarity clustering and natural product structure
Marcus A. Koch,Lars-Oliver Wittenberg,Sudipta Basu,Duraiswamy A. Jeyaraj,Eleni Gourzoulidou,Kerstin Reinecke,Alex Odermatt,Herbert Waldmann +7 more
TL;DR: Protein structure similarity clustering of the ligand-sensing cores of protein domains is proposed in conjunction with natural product guided compound library development as a synergistic approach for the identification of biologically prevalidated ligands with high fidelity.
Journal ArticleDOI
Dual-specificity phosphatases as targets for antineoplastic agents
TL;DR: It is hoped that this comprehensive overview of the salient developments in the biology and medicinal chemistry of dual-specificity phosphatases will stimulate further progress in the development of small-molecule inhibitors that could form the basis for a new class of target-directed therapeutic agents.
References
More filters
Journal ArticleDOI
Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
D. B. Dess,J. C. Martin +1 more
TL;DR: Conversion de cyclohexanol, octanol, alcool benzylique and des alcools dimethoxy-and trimethoxy benzyliques par oxydation avec le triacetoxy-1, 1, 1 benzoiodoxole-1 2 one-3
Journal ArticleDOI
Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications
Journal ArticleDOI
A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
TL;DR: In this paper, the authors described a new method for the catalytic enantioselective reduction of ketones to chiral secondary alcohols, where the stoichiometric reagent in the reduction is borane and the catalyst is a chiral oxazaborolidine such as 1 (0.05-0.1 molfmol of ketone).
Journal ArticleDOI
New synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketones
Journal ArticleDOI
Novel reagent system for converting a hydroxy-group into an iodo-group in carbohydrates with inversion of configuration. Part 2
Per J. Garegg,Bertil Samuelsson +1 more
TL;DR: In this article, isolated primary and secondary hydroxy-groups in carbohydrate derivatives are transformed into iodo-groups with inversion of configuration on treatment with either triphenylphosphine, iodine, and imidazole or triphensyl-phosphines and 2,4,5-tri-iodoimidazoles at elevated temperatures.