127258-20-2Relevant academic research and scientific papers
Efficient Preparation of Intermediates Corresponding to C22-C27 and C28-C34 of FK-506
Linde, II Robert G.,Egbertson, Melissa,Coleman, Robert S.,Jones, A. Brian,Danishefsky, Samuel J.
, p. 2771 - 2776 (2007/10/02)
Efficient large-scale preparations of aldehyde 2 and sulfone 3 representing the C22-C27 and C28-C34 potions of the immunosuppressant FK-506 (1) are descibed.
Total synthesis of FK506 and an FKBP probe reagent, (C8,C9-13C2)-FK506
Nakatsuka, Masashi,Ragan, John A.,Sammakia, Tarek,Smith, David B.,Uehling, David E.,Schreiber, Stuart L.
, p. 5583 - 5601 (2007/10/02)
Asymmetric syntheses of FK506 and (C8,C9-13C2)-FK506 are reported. The latter compound was designed to facilitate an investigation of the interactions between FK506 and its receptor, the recently discovered immunophilin, FKBP. The syntheses involved the preparation of intermediates 7-9 in nonracemic form; the key coupling reactions included a Cram-selective addition of the vinyl Grignard reagent derived from bromide 9 to aldehyde 8 and the addition of the lithioanion of phosphonamide 7 to aldehyde 51, followed by thermal elimination. Dithiane 65 was then hydrolyzed, and glycolic ester 6 (or 6*) was added via an aldol reaction that allowed the introduction of 13C labels at C8 and C9. Elaboration to FK506 proceeded via a Mukaiyama lactamization reaction and a selective deprotection/oxidation sequence, the efficiency of which was critically dependent upon the order of protecting group removal.
An Approach to the Cyclohexyl Moiety of the Immunosuppressive Agent FK-506
Pearson, Anthony J.,Roden, Brian A.
, p. 723 - 725 (2007/10/02)
Tricarbonyl(3-methoxycyclohexadienyl)iron hexafluorophosphate, which is readily prepared from 1,3-dimethoxybenzene, was treated with the enolate of methyl phenylsulphonylacetate to give an adduct which was decarboxylated and decomplexed to give 5-phenylsu
FK-506 SYNHETIC STUDIES. 3. AN EFFICIENT ASYMMETRIC SYNTHESIS OF THE C(24)-C(34) FRAGMENT OF FK-506, FR-900520, AND FR-900523
Smith, Amos B. III.,Hale, Karl J.,Laakso, Leif M.,Chen, Kwunmin,Riera, Antoni
, p. 6963 - 6966 (2007/10/02)
An efficient asymmetric synthesis of the C(24)-C(34) fragment of the FK-506 family of immunosuppressants has been achieved.
Studies Relating to the Synthesis of Immunosuppressive Agent FK-506: Synthesis of the Cyclohexyl Moiety via a Group-Selective Epoxidation
Schreiber, Stuart L.,Smith, David B.
, p. 9 - 10 (2007/10/02)
The asymmetric synthesis of the cyclohexyl moiety of FK-506 is reported.The absolute stereogenicity of the target subunit was derived from the catalytic asymmetric synthesis of an epoxide by the method of Sharpless.
