An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l-norvaline. Formal synthesis of clavalanine.

Jesus Ariza; Josep Font; Rosa M. Ortuño

doi:10.1016/0040-4039(91)85018-Z

An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l-norvaline. Formal synthesis of clavalanine.

Jesus Ariza, Josep Font, Rosa M. Ortuño

Department of Chemistry

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

22 Citations (Scopus)

Abstract

The title amino acid (2) has been synthesized for the first time in a seven-step sequence from D-ribonolactone, in 20% overall yield. Since the N-carbamoyl derivative of (2) in its γ-lactone form has been used to prepare clavalanine, a formal total synthesis of this antibiotic is derived. © 1991.

Original language	English
Pages (from-to)	1979-1982
Journal	Tetrahedron Letters
Volume	32
Issue number	17
DOIs	https://doi.org/10.1016/0040-4039(91)85018-Z
Publication status	Published - 22 Apr 1991

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title = "An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l-norvaline. Formal synthesis of clavalanine.",

abstract = "The title amino acid (2) has been synthesized for the first time in a seven-step sequence from D-ribonolactone, in 20% overall yield. Since the N-carbamoyl derivative of (2) in its γ-lactone form has been used to prepare clavalanine, a formal total synthesis of this antibiotic is derived. {\textcopyright} 1991.",

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AU - Font, Josep

AU - Ortuño, Rosa M.

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AB - The title amino acid (2) has been synthesized for the first time in a seven-step sequence from D-ribonolactone, in 20% overall yield. Since the N-carbamoyl derivative of (2) in its γ-lactone form has been used to prepare clavalanine, a formal total synthesis of this antibiotic is derived. © 1991.

U2 - 10.1016/0040-4039(91)85018-Z

DO - 10.1016/0040-4039(91)85018-Z

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 17

ER -

An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l-norvaline. Formal synthesis of clavalanine.

Abstract

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