Zhou Jingye, Snider Barry B
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Org Lett. 2007 May 24;9(11):2071-4. doi: 10.1021/ol0704338. Epub 2007 Apr 28.
Acid-catalyzed condensation of 2,6-dihydroxybenzoic acid 3 with ketal aldehyde 14 in methanol at 25 degrees C, followed by CH2N2 esterification, gave a 4:1:4:1 mixture of diastereomers 15b-18b in 60% yield. Equilibration of this mixture with TFA in CDCl3 provided tetracycle 15b (83% yield) with the complete skeleton of berkelic acid. A similar condensation at 0 degrees C afforded 15b-18b and a reduction product 19b, which was probably formed by a 1,5-hydride shift.
2,6 - 二羟基苯甲酸3与缩酮醛14在25℃的甲醇中进行酸催化缩合反应,随后进行重氮甲烷酯化反应,得到非对映异构体15b - 18b的4:1:4:1混合物,产率为60%。该混合物在CDCl₃中与三氟乙酸进行平衡反应,得到具有伯克酸完整骨架的四环化合物15b(产率83%)。在0℃下进行类似的缩合反应得到15b - 18b和一种还原产物19b,该还原产物可能是通过1,5 - 氢迁移形成的。