145625-08-7Relevant articles and documents
Unusual regiochemistry of cycloaddition of ketenes to (R)-2-tert-butyldihydrooxazole derivatives. A simple route towards enantiomerically pure functionalised α-aminocyclobutanones
Cagnon, Jose Renato,Le Bideau, Franck,Marchand-Brynaert, Jacqueline,Ghosez, Leon
, p. 2291 - 2294 (1997)
Ketenes have been found to cycloadd with (R)-2-tert-Butyldihydrooxazole 1 and 2 to yield predominantly regioisomers 4 resulting from steric control rather than electronic control. The cycloadditions provide a practical route to enantiomerically pure protected 2-amino-3-hydroxycyclobutanones.
Stereocontrolled α-alkylation of fully protected L-serine
Brunner, Martin,Saarenketo, Pauli,Straub, Thomas,Rissanen, Kari,Koskinen, Ari M. P.
, p. 3879 - 3883 (2004)
Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Total Synthesis of Tambromycin by Combining Chemocatalytic and Biocatalytic C?H Functionalization
Zhang, Xiao,King-Smith, Emma,Renata, Hans
supporting information, p. 5037 - 5041 (2018/03/27)
A combination of genomic and metabolomic approaches recently resulted in the identification of a nonribosomal tetrapeptide tambromycin, which possesses promising antiproliferative activity and several unusual structural features, including a densely substituted indole, a methyloxazoline ring, and an unusual pyrrolidine-containing amino acid called tambroline. In this work, we identify a concise synthetic route to access tambromycin, which relies on the strategic use of biocatalytic and chemocatalytic C?H functionalization methods to prepare two key precursors to the natural product in an efficient and scalable manner. The success of our study highlights the benefits of applying the principles of biocatalytic retrosynthesis as well as C?H functionalization logic to the synthesis of complex molecular scaffolds.
Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G
Fairhurst, Nathan W. G.,Mahon, Mary F.,Munday, Rachel H.,Carbery, David R.
supporting information; experimental part, p. 756 - 759 (2012/03/26)
The Ireland - Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.
Complementary syntheses of N,O-protected-(S)-2-methylserine on a multikilogram scale
Anson, Michael S.,Clark, Hugh F.,Evans, Paul,Fox, Martin E.,Graham, Jonathan P.,Griffiths, Natalie N.,Meek, Graham,Ramsden, James A.,Roberts, Alastair J.,Simmonds, Shaun,Walker, Matthew D.,Willets, Matthew
experimental part, p. 389 - 397 (2012/02/02)
Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with >99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic l-serine derivative under cryogenic conditions. The four-step telescoped process, starting from l-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3- oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.
Synthesis of enantiomerically pure α-amino-β-hydroxy- cyclobutanone derivatives and their transformations into polyfunctional three- and five-membered ring compounds
Ghosez, Léon,Yang, Gaoqiang,Cagnon, José Renato,Bideau, Franck Le,Marchand-Brynaert, Jacqueline
, p. 7591 - 7606 (2007/10/03)
Ketenes readily cycloadded to (R)-tert-butyldihydrooxazole 2a-d to yield enantiomerically pure bicyclic cyclobutanones. The cycloadditions proceeded with unusual regiochemistry giving predominantly or exclusively protected α-amino-β-hydroxycyclobutanone derivatives. The adducts could be converted into a variety of interesting enantiopure intermediates equipped with many functional groups: α-amino-β-hydroxy cyclopropane carboxylic acid derivatives, α-amino-β-hydroxy succinic acid derivatives, α-amino-β-hydroxy lactones and lactams derivatives.
A New Peptide Bond Surrogate: 2-Isoxazoline in Pseudodipeptide Chemistry
Kim, Byeang Hyean,Chung, Yong Jun,Keum, Gyochang,Kim, Jaheon,Kim, Kimoon
, p. 6811 - 6814 (2007/10/02)
The isoxazoline ring has been incorporated as a new peptide bond surrogate into pseudodipeptide.An easy and versatile general method for the preparation of pseudodipeptides is described.
