118949-52-3Relevant academic research and scientific papers
Isolation of an isomer of FK-506 from fermentation of Streptomyces tsukubaensis and its chemical synthesis from FK-506
Grassberger, Maximilian A.,Fehr, Theodor,Horvath, Amarylla,Schulz, Gerhard
, p. 413 - 430 (2007/10/02)
From the fermentation broth of Streptomyces tsukubaensis 9993 an isomer 2a of the immunosuppressant FK-506 1a was isolated as a minor metabolite. From NMR- and FAB-MS data follows that in 2a the size of the macrocycle is reduced by two carbon atoms due to
On the Remarkable Propensity for Carbon-Carbon Bond Cleavage Reactions in the C8-C10 Region of FK-506
Fisher, Matthew J.,Chow, Ken,Villalobos, Anabella,Danishefsky, Samuel J.
, p. 2900 - 2907 (2007/10/02)
It has been deduced from a series of transformations that formation of a tetrahedral intermediate at C9 in FK-506 occasions fragmentation of the C9-C10 bond by a retro-Claisen-like pathway or the C9-C8 bond by a benzilic acid type rearrangement.Reduction
Chemistry of tricarbonyl hemiketals and application of Evans' technology to the total synthesis of the immunosuppressant (-)-FK-506
Jones,Reamer,Desmond,Mills
, p. 2998 - 3017 (2007/10/02)
Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Application of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed.
Degradation and manipulations of the immunosuppressant FK506: Preparation of potential synthetic intermediates
Coleman, Robert S.,Danishefsky, Samuel J.
, p. 157 - 161 (2007/10/02)
Degradation of the immunosuppressant FK506 is described.
