Stereocontrolled Total Synthesis of (−)-Englerin A

…, Y Yokoi, J Ishihara, S Hatakeyama

文献索引：Takahashi, Keisuke; Komine, Keita; Yokoi, Yuichi; Ishihara, Jun; Hatakeyama, Susumi Journal of Organic Chemistry, 2012 ,  vol. 77,  # 17  p. 7364 - 7370

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被引用次数: 12

摘要

The total synthesis of (−)-englerin A, a potent and selective inhibitor of renal cancer cell lines, is described. The key feature includes the stereocontrolled construction of the cyclopentane structure by taking advantage of a base-promoted epoxynitrile cyclization. ... Our synthesis commenced with an eight-step preparation of epoxynitrile 8 from commercially available ketone 9 (Scheme 2). Thus, Baeyer–Villiger oxidation of 9,(12) DIBALH reduction of 10, and Wittig reaction ...