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Bicyclic Compounds Derived from Tartaric Acid and α‐Amino Acids (BTAas): Synthesis of New Molecular Scaffolds Derived from the Combination of ( R , R )‐Tartaric Acid and L ‐Serine
Author(s) -
Cini Nicoletta,
Machetti Fabrizio,
Menchi Gloria,
Occhiato Ernesto G.,
Guarna Antonio
Publication year - 2002
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 - 10.1002/1099-0690(200203)2002:5<873::aid-ejoc873>3.0.co;2-v
Subject(s) - chemistry , dipeptide , bicyclic molecule , tartaric acid , stereochemistry , octane , serine , hydroxymethyl , carboxylate , amino acid , organic chemistry , biochemistry , citric acid , enzyme
The synthesis of the new N ‐Fmoc‐protected dipeptide isoster methyl (1 S ,2 S ,5 S ,6 R )‐2 exo ‐hydroxymethyl‐7,8‐dioxa‐3‐azabicyclo[3.2.1]octane‐6 exo ‐carboxylate (BTS) has been achieved, starting from ( R , R )‐tartaric acid and O ‐benzyl‐ L ‐serine, in 11% overall yield after 9 steps. Interestingly, starting from the same α‐amino acid, it was also possible to prepare the 2 endo ‐substituted compound, formally derived from the combination of tartaric acid with D ‐serine. Each compound has a CH 2 OH functional group at C‐2, which is very useful for greater diversification of the 7,8‐dioxa‐3‐azabicyclo[3.2.1]octane‐6‐carboxylate (BTAa) dipeptide isosters. The oxidation of the C‐2 carbinol group in BTS, moreover, gave rise to a novel, conformationally constrained, α‐amino acid that may find application in peptidomimetic synthesis.