870465-58-0Relevant academic research and scientific papers
Efficient synthesis of [3H]-sanglifehrin A via selective oxidation/reduction of alcohols at C31 and C35
Wagner, Juergen,Andres, Hendrik,Rohrbach, Stefan,Wagner, Dieter,Oberer, Lukas,France, Julien
, p. 9588 - 9590 (2007/10/03)
Sanglifehrin A is a novel complex natural product showing strong immunosuppressive activity and remarkably high affinity for cyclophilin A. To assess its pharmacokinetic properties in vivo, an efficient synthetic route was developed to introduce a tritium
Total synthesis of the novel immunosuppressant sanglifehrin A
Nicolaou,Murphy,Barluenga,Ohshima,Wei,Xu,Gray,Baudoin
, p. 3830 - 3838 (2007/10/03)
The total synthesis of the novel immunosuppressant sanglifehrin A (SFA, 1) is described. The approach is flexible, convergent, and stereoselective. The use of Paterson's aldol methodology was pivotal for the preparation of the novel, highly substituted sp
Toward a Total Synthesis of the Immunosuppressant Sanglifehrin A. Preparation of Two Relay Compounds by Degradation and Their Use in the Reassembly of the Natural Product
Metternich, Rainer,Denni, Donatienne,Thai, Binh,Sedrani, Richard
, p. 9632 - 9639 (2007/10/03)
A potential relay route for the synthesis of the novel immunosuppressive agent sanglifehrin A (1) has been developed. Degradation of 1 by a sequence involving regioselective dihydroxylation of the C26,C27 double bond, followed by periodate cleavage of the resulting diol 4, afforded lactol 2 and macrocyclic aldehyde 3. Intramolecular ketal formation between the 1,3-diol and ketone functions present in 3 gave ketal-aldehyde 5. Lactol 2 was converted into sulfone 14 in four steps. The fragments 5 and 14 were reassembled, using the Julia-Kocienski olefination procedure, to afford intermediate 15, which was converted back to sanglifehrin A (1) after two deprotection steps.
