An article Asymmetric Diels-Alder reaction of 3-(acyloxy)acryloyl oxazolidinones: optically active synthesis of a high-affinity ligand for potent HIV-1 protease inhibitors WOS:000503782700038 published article about CYCLOADDITION REACTIONS; ENANTIOSELECTIVE CYCLOADDITION; CATALYSTS; BACKBONE; DESIGN in [Ghosh, Arun K.; Grillo, Alessandro; Kovela, Satish; Brindisi, Margherita] Purdue Univ, Dept Chem, 560 Oval Dr, W Lafayette, IN 47907 USA; [Ghosh, Arun K.] Purdue Univ, Dept Med Chem & Mol Pharmacol, 560 Oval Dr, W Lafayette, IN 47907 USA; [Brindisi, Margherita] Univ Naples Federico II, Dept Excellence Pharm, Naples, Italy in 2019.0, Cited 29.0. The Name is 4-Nitrobenzoic acid. Through research, I have a further understanding and discovery of 62-23-7. Category: phthalazines
We describe here our investigation of the asymmetric Diels-Alder reaction of chiral 3-(acyloxy)acryloyl oxazolidinones as dienophiles in various Lewis-acid promoted reactions with cyclopentadiene. The resulting highly functionalized cycloadducts are useful intermediates for the synthesis, particularly for the optically active synthesis of 6-5-5 tricyclic hexahydro-4H-3,5-methanofuro[2,3-b]pyranol (3) with five contiguous chiral centers. This stereochemically defined crown-like heterocyclic derivative is an important high affinity ligand for a variety of highly potent HIV-1 protease inhibitors. Among the various dienophiles and Lewis acid-mediated reactions surveyed, 3-(4-methoxybenzoyl)acryloyl oxazolidinone as the dienophile and diethylaluminum chloride as the Lewis-acid provided the desired endo product with excellent diastereoselectivity. The cycloaddition was carried out in multi-gram scale and the cycloadduct was efficiently converted to alcohol 3 with high enantiomeric purity. The optically active ligand was then transformed into potent HIV-1 protease inhibitor 2.
Category: phthalazines. Welcome to talk about 62-23-7, If you have any questions, you can contact Ghosh, AK; Grillo, A; Kovela, S; Brindisi, M or send Email.
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