127793-69-5Relevant academic research and scientific papers
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.
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
MACROLIDES AND METHODS OF THEIR PREPARATION AND USE
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Paragraph 00653, (2014/10/18)
Provided herein are methods of preparing macrolides by the coupling of an eastern and western half, followed by macrocyclization, to provide macrolides, including both known and novel macrolides. Intermediates in the synthesis of macrolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using the inventive macrolides are also provided. A general diastereoselective aldol methodology used in the synthesis of the western half is further provided.
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.
Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy
Ugele, Markus,Maier, Martin E.
supporting information; experimental part, p. 2633 - 2641 (2010/05/01)
The alkaloid tyroscherin (2), which contains a vicinal anti-amino alcohol subunit was prepared from 4-hydroxyphenylpropionic acid (5) and meso-diol 9. After desymmetrization of diol 9 and suitable protecting group manipulations, one terminus was extended via a Claisen rearrangement giving rise to enoate ent-15. The missing carbon on the other end could be incorporated using MeMgCl/CuBr·SMe2 leading eventually to aldehyde ent-22. The acylated oxazolidinone 32 derived from acid 5 and aldehyde ent-22 were combined in an aldol reaction. A subsequent Curtius rearrangement on the carboxylic group furnished the amino function of tyroscherin (2). In a proof of concept study the same strategy was used to prepare tyroscherin analog 28.
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
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
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
