Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone

Jesús Ariza; Miguel Díaz; Josep Font; Rosa M. Ortuño

doi:10.1016/S0040-4020(01)85821-X

Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone

Jesús Ariza, Miguel Díaz, Josep Font, Rosa M. Ortuño

Departament de Química

Producció científica: Contribució a revista › Article › Recerca › Avaluat per experts

18 Cites (Scopus)

Resum

Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine. © 1993.

Idioma original	Anglès
Pàgines (de-a)	1315-1326
Revista	Tetrahedron
Volum	49
Número	6
DOIs	https://doi.org/10.1016/S0040-4020(01)85821-X
Estat de la publicació	Publicada - 5 de febr. 1993

Accés al document

10.1016/S0040-4020(01)85821-X

Com citar-ho

@article{1951b71a62a94bd4bf3aa98423317665,

title = "Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone",

abstract = "Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine. {\textcopyright} 1993.",

author = "Jes{\'u}s Ariza and Miguel D{\'i}az and Josep Font and Ortu{\~n}o, {Rosa M.}",

year = "1993",

month = feb,

day = "5",

doi = "10.1016/S0040-4020(01)85821-X",

language = "English",

volume = "49",

pages = "1315--1326",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "6",

}

TY - JOUR

T1 - Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone

AU - Ariza, Jesús

AU - Díaz, Miguel

AU - Font, Josep

AU - Ortuño, Rosa M.

PY - 1993/2/5

Y1 - 1993/2/5

N2 - Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine. © 1993.

AB - Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine. © 1993.

U2 - 10.1016/S0040-4020(01)85821-X

DO - 10.1016/S0040-4020(01)85821-X

M3 - Article

SN - 0040-4020

VL - 49

SP - 1315

EP - 1326

JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -

Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone

Resum

Accés al document

Fingerprint

Com citar-ho