Synthetic approaches to either homochiral or achiral derivatives of 3-hydroxy-2(5H)-furanone (isotetronic acid)

Joaquim Bigorra; Josep Font; Cristina Ochoa de Echagüen; Rosa M. Ortuño

doi:10.1016/S0040-4020(01)81841-X

Synthetic approaches to either homochiral or achiral derivatives of 3-hydroxy-2(5H)-furanone (isotetronic acid)

Joaquim Bigorra, Josep Font, Cristina Ochoa de Echagüen, Rosa M. Ortuño

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

21 Citations (Scopus)

Abstract

Several title compounds were synthesized according to new methods based either on the use of D-ribonolactone as a chiral precursor or on the cyclization of 2,4-dioxopentanoic acid as a suitable achiral precursor. Base-induced elimination and subsequent acid-promoted ring contraction is an efficient protocol for the preparation of isotetronic acids from 2-O-alkyl-3,4-O-benzylidene-D-ribono-1,5-lactone derivatives. © 1993.

Original language	English
Pages (from-to)	6717-6728
Journal	Tetrahedron
Volume	49
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4020(01)81841-X
Publication status	Published - 23 Jul 1993

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title = "Synthetic approaches to either homochiral or achiral derivatives of 3-hydroxy-2(5H)-furanone (isotetronic acid)",

abstract = "Several title compounds were synthesized according to new methods based either on the use of D-ribonolactone as a chiral precursor or on the cyclization of 2,4-dioxopentanoic acid as a suitable achiral precursor. Base-induced elimination and subsequent acid-promoted ring contraction is an efficient protocol for the preparation of isotetronic acids from 2-O-alkyl-3,4-O-benzylidene-D-ribono-1,5-lactone derivatives. {\textcopyright} 1993.",

author = "Joaquim Bigorra and Josep Font and {de Echag{\"u}en}, {Cristina Ochoa} and Ortu{\~n}o, {Rosa M.}",

year = "1993",

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T1 - Synthetic approaches to either homochiral or achiral derivatives of 3-hydroxy-2(5H)-furanone (isotetronic acid)

AU - Bigorra, Joaquim

AU - Font, Josep

AU - de Echagüen, Cristina Ochoa

AU - Ortuño, Rosa M.

PY - 1993/7/23

Y1 - 1993/7/23

N2 - Several title compounds were synthesized according to new methods based either on the use of D-ribonolactone as a chiral precursor or on the cyclization of 2,4-dioxopentanoic acid as a suitable achiral precursor. Base-induced elimination and subsequent acid-promoted ring contraction is an efficient protocol for the preparation of isotetronic acids from 2-O-alkyl-3,4-O-benzylidene-D-ribono-1,5-lactone derivatives. © 1993.

AB - Several title compounds were synthesized according to new methods based either on the use of D-ribonolactone as a chiral precursor or on the cyclization of 2,4-dioxopentanoic acid as a suitable achiral precursor. Base-induced elimination and subsequent acid-promoted ring contraction is an efficient protocol for the preparation of isotetronic acids from 2-O-alkyl-3,4-O-benzylidene-D-ribono-1,5-lactone derivatives. © 1993.

U2 - 10.1016/S0040-4020(01)81841-X

DO - 10.1016/S0040-4020(01)81841-X

M3 - Article

VL - 49

SP - 6717

EP - 6728

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 30

ER -