The Synthesis of cis- and trans-Fused Bicyclic Sugar Amino Acids

Four isomeric bicyclic sugar amino acids (SAAs) were prepared from α‐acetylenic‐C‐glucoside 6 by employing a Petasis olefination and a ring‐closing metathesis (RCM) as key steps. The applicability of the resulting SAAs in solid‐phase peptide synthesis was demonstrated by the synthesis of tetrapeptid...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2006-09, Vol.2006 (17), p.3877-3886
Main Authors: Risseeuw, Martijn D. P., Grotenbreg, Gijsbert M., Witte, Martin D., Tuin, Adriaan W., Leeuwenburgh, Michiel A., Van der Marel, Gijsbert A., Overkleeft, Herman S., Overhand, Mark
Format: Article
Language:English
Subjects:
Petasis olefination
Pyranopyran
Ring-closing metathesis
Sugar amino acids
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Summary:Four isomeric bicyclic sugar amino acids (SAAs) were prepared from α‐acetylenic‐C‐glucoside 6 by employing a Petasis olefination and a ring‐closing metathesis (RCM) as key steps. The applicability of the resulting SAAs in solid‐phase peptide synthesis was demonstrated by the synthesis of tetrapeptide 36. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600228