Stereoselective Synthesis and Absolute Configuration Determination of Xylariolide A

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Stereoselective Synthesis and Absolute Configuration Determination of Xylariolide A

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Title: Stereoselective Synthesis and Absolute Configuration Determination of Xylariolide A
Author: Botubol Ares, José Manuel; Macías Sánchez, Antonio José; González Collado, Isidro; Hernández Galán, Rosario
Departments: Química Orgánica
xmlui.dri2xhtml.METS-1.0.item-source: European Journal of Organic Chemistry 2013, 2420–2427
Abstract: The asymmetric synthesis of the antibacterial and antitumoral natural compound xylariolide A (1) and five stereoisomers has been achieved. The strategy is based on the onepot epoxidation/lactonisation or dihydroxylation/lactonisation of the hypothetical biosynthetic intermediate xylarioic A acid (8). The absolute configuration of xylariolide A was thus determined to be 3R,4S,5R,1 R,2 R after the synthesis of 1, two epimers, i.e., 1 -epi-xylariolide A (3) and 2 -epi-xylariolide A (4), and three more diastereoisomers 5–7.
Subject: Natural products ; Total synthesis ; Asymmetric synthesis ; Configuration determination ; Medicinal chemistry ; Lactones.
Handle: http://hdl.handle.net/10498/20572
Date: 2013

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