cas 173065-16-2, (S)-2,2-Dimethyl-3-(N-Boc)-4-ethynyl-oxazolidine

Articles about 173065-16-2Total 12 be found

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid
The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.
Boibessot, Thibaut,Bénimèlis, David,Jean, Marion,Benfodda, Zohra,Meffre, Patrick
supporting information
p. 2685 - 2688
(2016/11/30)

Total synthesis of the COPD biomarker desmosine via stepwise Sonogashira cross-coupling reactions
Desmosine, a COPD biomarker and elastin crosslinker, is a tetrasubstituted pyridinium amino acid. In this paper, the total synthesis of desmosine is described utilizing stepwise and regioselective palladium-catalyzed Sonogashira cross-coupling reactions o
Yamada, Haruka,Hayashi, Takahiro,Usuki, Toyonobu
p. 673 - 683
(2015/06/25)

Total synthesis of COPD biomarker desmosine that crosslinks elastin
Desmosine, a crosslinking amino acid of elastin, is an attractive biomarker for diagnosis of chronic obstructive pulmonary disease (COPD). In this study, the first total synthesis of (+)-desmosine was achieved in 11% overall yield in 13 steps utilizing st
Usuki, Toyonobu,Yamada, Haruka,Hayashi, Takahiro,Yanuma, Hiroto,Koseki, Yohei,Suzuki, Noriyuki,Masuyama, Yoshiro,Lin, Yong Y.
supporting information; experimental part
p. 3233 - 3235
(2012/04/10)

Total synthesis of tryprostatins A and B
Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fuerstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.
Yamakawa, Takayuki,Ideue, Eiji,Iwaki, Yuzo,Sato, Ayumu,Tokuyama, Hidetoshi,Shimokawa, Jun,Fukuyama, Tohru
experimental part
p. 6547 - 6560
(2011/09/20)

1,2-diastereoselective C-C bond-forming reactions for the synthesis of chiral β-branched α-amino acids
SN2′ sequences have been employed for the synthesis of β-branched α-amino acids using 1,2-diastereocontrol for forming C-C bonds. An oxazolidine fragment derived from Garner's aldehyde provides the handle for facial discrimination and acts as a
Spangenberg, Thomas,Schoenfelder, Angele,Breit, Bernhard,Mann, Andre
experimental part
p. 6005 - 6018
(2011/02/25)

Total synthesis of tryprostatins a and b
A reasonable approach to the radical: The establishment of reliable conditions for the radical-mediated construction of indoles enabled the highly efficient synthesis of tryprostatins A and B. Use of the radical initiator 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) has allowed to carry out the radical cyclization at just 30°C, thereby suppressing the formation of by-products. Copyright
Yamakawa, Takayuki,Ideue, Eiji,Shimokawa, Jun,Fukuyama, Tohru
supporting information; experimental part
p. 9262 - 9265
(2011/02/25)

A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids
A method for the synthesis of β3-amino acids starting from α-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give β3-amino acids, β3-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into β3-amino acids may not require purification of the intermediate products but a work-up and isolation procedure of crude materials.
Temperini, Andrea,Capperucci, Antonella,Degl'Innocenti, Alessandro,Terlizzi, Raffaella,Tiecco, Marcello
supporting information; experimental part
p. 4121 - 4124
(2010/08/20)

Total synthesis of (+)-asperazine
The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is ex
Govek, Steven P.,Overman, Larry E.
p. 8499 - 8513
(2008/02/09)

A convenient scalable one-pot conversion of esters and Weinreb amides to terminal alkynes
Esters and amides undergo reduction to the corresponding aldehydes using DIBAL-H followed by same pot conversion to terminal alkynes utilizing the Bestmann-Ohira reagent in good to excellent yields. Additionally chiral nonracemic substrates undergo this transformation with complete preservation of stereochemical integrity.
Dickson, Hamilton D.,Smith, Stephon C.,Hinkle, Kevin W.
p. 5597 - 5599
(2007/10/03)

Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde
A simple, efficient and practical synthesis of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine (ethynylglycine synthon) is described. The method involves in situ formation of dimethyl 1-diazo-2-oxopropyl phosphonate from dimethyl 2-oxopropyl phosphonate and 4-acetamidobenzene sulfonyl azide and one-pot reaction on Garner's aldehyde. The reaction has been extended to other aminoaldehydes.
Meffre, Patrick,Hermann, Sébastien,Durand, Philippe,Reginato, Gianna,Riu, Antonella
p. 5159 - 5162
(2007/10/03)

Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A New Regio- And Stereoselective Strategy to δ-Functionalized β-Amino Alcohols
An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.
Reginato, Gianna,Mordini, Alessandro,Caracciolo, Massimo
p. 6187 - 6192
(2007/10/03)

Stereoselective synthesis of (R)-(-)-2,2-dimethyl-3-t-butoxycarbonyl-4-ethynyloxazolidine: A chiral building block for the synthesis of a new class of substituted alkynes
(R)-(-)-2,2-Dimethyl-3-t-butoxycarbonyl-4-ethynyl-oxazolidine (3a) has been prepared in good yield from chiral aminoaldehyde (4) through a two step procedure. Metalation of compound (3a) and subsequent reaction with electrophiles has been investigated lea
Reginato, Gianna,Mordini, Alessandro,Degl'Innocenti, Alessandro,Caracciolo, Massimo
p. 8275 - 8278
(2007/10/02)