Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA.
Org Lett. 2011 Dec 16;13(24):6592-5. doi: 10.1021/ol203041b. Epub 2011 Nov 22.
A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a β-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 μM).
已实现（R）-和（S）-fridamycin E 的从头不对称合成。该完全线性路线仅需从商业上可获得的起始原料进行九步反应（总收率为 16%）。关键转化包括 Claisen 重排、Sharpless 双羟化和钴催化环氧化物羰基化，以得到β-内酯中间体。使用两种大肠杆菌菌株测定了两种对映体的抗菌活性，天然（R）-对映体对革兰氏阳性样 imp 菌株显示出显著的抑制作用（MIC = 8 μM）。
