738535-66-5Relevant academic research and scientific papers
Solid-phase synthesis of peptides containing bulky dehydroamino acids
Jiang, Jintao,Luo, Shi,Castle, Steven L.
, p. 3311 - 3313 (2015)
A method of incorporating bulky α,β-dehydroamino acids such as dehydrovaline and dehydroethylnorvaline into peptides via solid-phase peptide synthesis is reported. The key step involves ring opening of an azlactone (i.e., oxazolone) containing the dehydro
Convergent Total Synthesis of Yaku'amide A
Cai, Yu,Ma, Zhiwei,Jiang, Jintao,Lo, Concordia C. L.,Luo, Shi,Jalan, Ankur,Cardon, Joseph M.,Ramos, Alexander,Moyá, Diego A.,Joaquin, Daniel,Castle, Steven L.
, p. 5162 - 5167 (2021/02/01)
Total synthesis of the anticancer peptide natural product yaku'amide A is reported. Its β-tert-hydroxy amino acids were prepared by regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecific construction of the E- and Z-ΔIle residues was accomplished through a one-pot reaction featuring anti dehydration, azide reduction, and O→N acyl transfer. Alkene isomerization was negligible during this process. These methods enabled a highly convergent and efficient synthetic route to the natural product.
SOLID-PHASE SYNTHESIS OF PEPTIDES CONTAINING BULKY DEHYDROAMINO ACIDS
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Paragraph 00126, (2016/06/28)
Methods of incorporating bulky α,β-dehydroamino acids such as dehydrovaline and dehydroethylnorvaline into peptides via solid-phase peptide synthesis and the resulting peptide compositions is reported. The synthesis method involves using azlactone interme
Regioselective base-free intermolecular aminohydroxylations of hindered and functionalized alkenes
Ma, Zhiwei,Naylor, Bradley C.,Loertscher, Brad M.,Hafen, Danny D.,Li, Jasmine M.,Castle, Steven L.
, p. 1208 - 1214 (2012/03/11)
Regioselective base-free intermolecular aminohydroxylations of functionalized trisubstituted and 1,1-disubstituted alkenes employing benzoyloxycarbamate 3a and catalytic OsO4 are described. In all cases, the more substituted alcohol isomer is f
