129032-45-7Relevant academic research and scientific papers
Studies directed towards the total synthesis of polyether antibiotic ionomycin: Asymmetric synthesis of fragments C(24)-C(32) and C(1)-C(23)
Yadav,Yadav, Nagendra Nath,Subba Reddy
, p. 7539 - 7549 (2015/09/07)
A convergent and stereoselective approach for the synthesis of C1-C23 and C24-C32 segments of polyether antibiotic, ionomycin has been achieved. The key steps involved in this approach are the elaboration of two advanced fragments from a common precursor
Unexpected stereochemical tolerance for the biological activity of tyroscherin
Tae, Hyun Seop,Hines, John,Schneekloth, Ashley R.,Crews, Craig M.
, 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.
An asymmetric hydrogenation route to (-)-Spongidepsin
Zhu, Ye,Loudet, Aurore,Burgess, Kevin
supporting information; experimental part, p. 4392 - 4395 (2010/12/18)
Figure Presented. (-)-Spongidepsin 1, a cytotoxic marine natural product, was prepared via two iridium-catalyzed hydrogenation reactions; both were highly stereoselective, giving convenient access to pivotal intermediates. This synthesis was modified to g
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
Formal total synthesis of (-)-spongidepsin
Chandrasekhar,Yaragorla,Sreelakshmi,Reddy, Ch. Raji
, p. 5174 - 5183 (2008/12/20)
The formal total synthesis of (-)-spongidepsin is described. Three fragments I, II, and III were first prepared from readily available starting materials and then assembled to the target compound. The key steps involved in the synthesis are asymmetric α-hydroxylation, Ender's alkylation, and ring-closing metathesis reactions. An alternative route for the fragment II is also achieved involving Sharpless asymmetric epoxidation and Gilman's alkylation as key reactions.
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
Total synthesis and structural assignment of spongidepsin through a stereodivergent ring-closing-metathesis strategy
Chen, Jiehao,Forsyth, Craig J.
, p. 2148 - 2152 (2007/10/03)
Eight diastereomeric probes (1) were generated to synthesize the novel, anti-proliferative marine natural product spongidepsin (2) and to determine its absolute stereochemistry. A key step was the formation of the macrocycle by ring-closing metathesis.
Assignment of absolute stereochemistry and total synthesis of (-)-spongidepsin
Ghosh, Arun K.,Xu, Xiaoming
, p. 2055 - 2058 (2007/10/03)
Equation presented. An enantioselective total synthesis of (-)-spongidepsin (2) and elucidation of the absolute stereochemistry of its four stereocenters are described. Spongidepsin (2), a 13-membered depsipeptide isolated from the Vanuatu marine sponge S
Acyclic diastereoselective synthesis using tartrate ester modified crotylboronates. Double asymmetric reactions with α-methyl chiral aldehydes and synthesis of the C(19)-C(29) segment of rifamycin S
Roush, William R.,Palkowitz, Alan D.,Ando, Kaori
, p. 6348 - 6359 (2007/10/02)
Double asymmetric reactions of the tartrate ester modified crotylboronates 1 and 2 and α-methyl chiral aldehydes are described. The reactions of the appropriate enantiomers of 1 and 2 with β-alkoxy-α-methylpropionaldehydes 11 provide adducts 12, 13, and 1
