210765-06-3Relevant academic research and scientific papers
Chiral and stereoselective total synthesis of novel immunosuppressant FR65814 from D-glucose
Amano, Seiji,Ogawa, Noriko,Ohtsuka, Masami,Chida, Noritaka
, p. 2205 - 2224 (2007/10/03)
The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.
Total synthesis and absolute configuration of FR65814
Amano, Seiji,Ogawa, Noriko,Ohtsuka, Masami,Ogawa, Seiichiro,Chida, Noritaka
, p. 1263 - 1264 (2007/10/03)
The chiral and highly stereoselective synthesis of FR658141, a novel immunosuppressant, starting from D-glucose is described; this first total synthesis fully confirms the proposed structure of 1.
