Synthesis of the revised structure of acortatarin A
A novel Maillard-type condensation between a primary amine derived from D-mannitol and a dihydropyranone, was used as a key step to access the unusual morpholine-spiroketal acortatarin A. The synthetic approach also enabled access to a C-2 analogue of acortatarin A, and can be used for the synthesis of related 2-formylpyrrole natural products.
Geng, Hui Min,Stubbing, Louise A.,Li-Yang Chen, Jack,Furkert, Daniel P.,Brimble, Margaret A.
p. 6227 - 6241
(2015/03/30)
A convergent synthesis of the 2-formylpyrrole spiroketal natural product acortatarin A
A concise and flexible synthesis of the morpholine-spiroketal natural product acortatarin A, isolated from the traditional Chinese medicine Acorus tatarinowii, is reported. The key step involves a Maillard-type condensation of an amine derived from d-mannitol with a dihydropyranone. The approach also enables access to analogues of acortatarin A for biological evaluation and can be applied to the synthesis of related 2-formylpyrrole natural products. Georg Thieme Verlag Stuttgart . New York.
Geng, Huimin,Chen, Jack L.Y.,Furkert, Danielp.,Jiang, Shende,Brimble, Margaret A.
p. 855 - 858
(2012/05/20)
An efficient and enantioselective total synthesis of naturally occurring L-783277
Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.
Choi, Hwan Geun,Son, Jung Beom,Park, Dong-Sik,Ham, Young Jin,Hah, Jung-Mi,Sim, Taebo
scheme or table
p. 4942 - 4946
(2011/01/04)
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