Practical enantioselective synthesis of a homotyrosine derivative and (R, R)-4-propyl-9-hydroxynaphthoxazine, a potent dopamine agonist

…, WF Shukis, AW Wood, JR Colleluori

文献索引：Melillo, David G.; Larsen, Robert D.; Mathre, David J.; Shukis, William F.; Wood, Alfred W.; Colleluori, Joseph R. Journal of Organic Chemistry, 1987 , vol. 52, # 23 p. 5143 - 5150

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被引用次数: 68

摘要

Two enantioselective routes were developed to prepare chiral amino acid derivative 4. The key step in the first route was catalytic hydrogenation of acrylate derivative 3 using chiral rhodium catalysts. In the second route the key step was acylation of 2-chloroanisole with (R)- aspartic anhydride (8), wherein chlorine acta as a removable directing group. Cyclization of (R)-homotyrosine 4b to tetxalone 13 and reduction to tetraloll4 occurred with preservation ...