Total Synthesis of Carba-d-fructofuranose via a Novel Metathesis Reaction

Total Synthesis of Carba-d-fructofuranose via a Novel Metathesis Reaction

Carba-d-fructofuranose 2b was synthesized in 11 steps (45%), from 2,3,5-tri-O-benzyl-d-arabinofuranose 5 using a ring closing metathesis. Schrock's catalyst was employed on the unique substituted diene synthon 4 to furnish the pentahydroxlated cyclopentene 3. Hydrogenation afforded 2b.

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Veröffentlicht in:Organic letters 1999-11, Vol.1 (9), p.1463-1465
Hauptverfasser: Seepersaud, Mohindra, Al-Abed, Yousef
Format: Artikel
Sprache:eng
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Zusammenfassung:Carba-d-fructofuranose 2b was synthesized in 11 steps (45%), from 2,3,5-tri-O-benzyl-d-arabinofuranose 5 using a ring closing metathesis. Schrock's catalyst was employed on the unique substituted diene synthon 4 to furnish the pentahydroxlated cyclopentene 3. Hydrogenation afforded 2b.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990275n