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The Synthesis of cis ‐ and trans ‐Fused Bicyclic Sugar Amino Acids
Author(s) -
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
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600228
Subject(s) - chemistry , bicyclic molecule , tetrapeptide , ring closing metathesis , metathesis , stereochemistry , sugar , salt metathesis reaction , combinatorial chemistry , organic chemistry , peptide , biochemistry , polymerization , polymer
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)