Stereoselective Synthesis and Absolute Configuration Determination of Xylariolide A
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Author/sBotubol Ares, José Manuel; Macías Sánchez, Antonio José; González Collado, Isidro; Hernández Galán, Rosario
SourceEuropean Journal of Organic Chemistry 2013, 2420–2427
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.