A total synthesis of the epoxyquinone natural product cytosporin D

Vannada, Jagadeshwar and Niehues, Lennart and Koenig, Burkhard and Mehta, Goverdhan (2013) A total synthesis of the epoxyquinone natural product cytosporin D. TETRAHEDRON, 69 (30). pp. 6034-6040. ISSN 0040-4020,

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Abstract

A synthesis of epoxyquinone natural product cytosporin D from the readily available Diels-Alder adduct of cyclopentadiene and 2-prenyl-p-benzoquinone, has been accomplished. This approach leverages the stereochemical predisposition of the norbornyl-fused systems towards convex face reactivity as an enabler for the stereoselective construction of the pyran ring. (C) 2013 Elsevier Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: ENANTIOSELECTIVE TOTAL-SYNTHESIS; NF-KAPPA-B; CONVERTING-ENZYME INHIBITORS; UBIQUITIN-ACTIVATING ENZYME; FARROWIA SP. E-1941; BIOLOGICAL-PROPERTIES; FUNGAL METABOLITES; BUILDING-BLOCKS; FLUOSTATIN-C; DIMER; Epoxyquinone natural products; Diels-Alder reaction; Stereoselective reduction; Wittig olefination; Oxycylization
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 06 Apr 2020 07:19
Last Modified: 06 Apr 2020 07:19
URI: https://pred.uni-regensburg.de/id/eprint/16348

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