Organic letters

Remote stereocontrol in [3, 3]-sigmatropic rearrangements: application to the total synthesis of the immunosuppressant mycestericin G

NWG Fairhurst, MF Mahon, RH Munday…

文献索引：Fairhurst, Nathan W. G.; Mahon, Mary F.; Munday, Rachel H.; Carbery, David R. Organic Letters, 2012 , vol. 14, # 3 p. 756 - 759

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被引用次数: 17

摘要

The Ireland–Claisen [3, 3]-sigmatropic rearrangement has been used to access biologically important β, β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.