128778-24-5Relevant academic research and scientific papers
Formal synthesis of borrelidin: A highly enantio- and diastereoselective access to the Morken's C2-C12 intermediate
Gembus, Vincent,Karmazin, Lydia,Uguen, Daniel,Zoller, Thomas
supporting information, p. 359 - 380 (2019/02/25)
In contrast to methyl and isobutyl phenyl sulfone, condensing under basic conditions higher alkyl sulfones and trans-2,3-epoxy-butanol 13c (or its O-benzyl and O-silyl derivatives) proved unfeasible, a difficulty that was overcome by using mono ethers of trans-2,3-epoxy-butane-1,4-diol 35c as the electrophilic reagents. Thus, adding excess BuLi to a mixture of the benzyl ether 35b and sulfone ent-12a, a stereodiad sulfone prepared in pure state from the R-Roche ester, via the O-trityloxy-sulfone ent-12c (X-ray), gave, after elimination by column chromatography of the side-formed regioisomer, a diolsulfone that was next converted to sulfone 20 by means of conventional functional-group modifications. Reacting like-wise this sulfone with the parent O-PMB derivative 35a, and then proceeding to the same purification process and function adjustment, delivered the title fragment in virtually pure state.
Total syntheses of rubiginone A2, C2, and fujianmycin A
Vanga, Devendar G.,Kaliappan, Krishna P.
, p. 12716 - 12722 (2014/04/03)
The total syntheses of rubiginone A2, C2 and fujianmycin A are described. The synthesis involves Diels-Alder/aromatization and photo chemical reactions as key steps to construct the tetracyclic frame of benz[a]anthraquinone skeleton.
Total synthesis of (+/-)-monomorine I and (+/-)-indolizidine 195B by an aza-[2,3]-Wittig rearrangement of a vinylaziridine.
Somfai,Jarevang,Lindstroem,Svensson
, p. 1024 - 1029 (2007/10/03)
A novel synthesis of (+/-)-monomorine I (1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be converted into the target alkaloids by reductive amination (1:2 1.5:1).
The opening of trans-2-3-epoxy-1-butanol derivatives with organometallic reagents
Skrydstrup, Troels,Benechie, Michel,Khuong-Huu, Francoise
, p. 7145 - 7148 (2007/10/02)
The opening of trans-2-3-epoxy-butan-1-ol derivatives with various organometallic reagents was studied to find the best conditions necessary to obtain convenient yields and regioselectivities for their application in natural product synthesis.
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.
Electrophilic Sulphenylation of Silyl Ketene Acetals Derived from 3-Hydroxyesters. Diastereoselective Synthesis of Protected Epoxyalcohols
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica,Thea, Sergio
, p. 1683 - 1686 (2007/10/02)
Anti-3-Hydroxy-2-phenylsulphenyl esters are stereoselectively synthesized by reaction between silyl ketene acetals and phenyl sulphenyl chloride.Subsequent elaboration leads to protected epoxyalcohols.
