Stereoselective Synthesis of d-Desosamine and Related Glycals via Tungsten-Catalyzed Alkynol Cycloisomerization

Stereoselective Synthesis of d-Desosamine and Related Glycals via Tungsten-Catalyzed Alkynol Cycloisomerization

Stereoselective synthesis of d-desosamine diacetate ester (iii, R = Ac) was achieved from the glycal (ii) generated by tungsten carbonyl-catalyzed cycloisomerization of the corresponding amino-alkynol (i). A wide variety of N-substituents (R, R‘) are compatible with the cycloisomerization, provided...

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Veröffentlicht in:Organic letters 2004-05, Vol.6 (10), p.1601-1603
Hauptverfasser: Davidson, Mary H, McDonald, Frank E
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Amino Sugars - chemical synthesis
Catalysis
Cyclization
Molecular Structure
Stereoisomerism
Tungsten - chemistry
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Zusammenfassung:Stereoselective synthesis of d-desosamine diacetate ester (iii, R = Ac) was achieved from the glycal (ii) generated by tungsten carbonyl-catalyzed cycloisomerization of the corresponding amino-alkynol (i). A wide variety of N-substituents (R, R‘) are compatible with the cycloisomerization, provided that at least one R or R‘ is an acyl derivative.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049630m