1001208-19-0Relevant articles and documents
Stereoselective synthesis of fully functionalized acyclic core of Tianchimycin A
Yamini, Vanipenta,Ghosh, Subhash
, p. 301 - 313 (2017/12/06)
A highly convergent synthetic approach towards the macrolactone polyketide tianchimycin A is described. Notable features of our synthetic approach include highly stereoselective Myers alkylation, substrate controlled anti aldol reaction, and Masamune-Roush olefination.
Unexpected stereochemical tolerance for the biological activity of tyroscherin
Tae, Hyun Seop,Hines, John,Schneekloth, Ashley R.,Crews, Craig M.
supporting information; scheme or table, p. 1708 - 1713 (2011/04/22)
Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules.
Total synthesis and biological evaluation of tyroscherin
Tae, Hyun Seop,Hines, John,Schneekloth, Ashley R.,Crews, Craig M.
supporting information; experimental part, p. 4308 - 4311 (2010/12/20)
Figure Presented. The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. Th
Evolution of the total synthesis of (-)-Okilactomycin exploiting a tandem oxy-cope rearrangement/oxidation, a petasis-ferrier union/rearrangement, and ring-closing metathesis
Smith, Amos B. III,Bosanac, Todd,Basu, Kallol
supporting information; experimental part, p. 2348 - 2358 (2009/07/30)
An effective, asymmetric total synthesis of the antitumor antibiotic (-)-okilactomycin (1), as well as assignment of the absolute configuration,has been achieved exploiting a convergent strategy. Highlights of the s ynthesis include a diastereoselective o
Total synthesis of (-)-okilactomycin
Smith III, Amos B.,Basu, Kallol,Bosanac, Todd
, p. 14872 - 14874 (2008/09/20)
A highly convergent synthesis of (-)-okilactomycin is described. Key reactions of this synthesis include a strategy-level diastereoselective oxy-Cope rearrangement/oxidation sequence, a Petasis-Ferrier union/rearrangement tactic, and an efficient RCM reac
