Stereoselective total synthesis of (-)-galantinic acid

Synlett

Volumn , Issue 10, 2006, Pages 1580-1582

  Bethuel, Yann ^a   Gademann, Karl ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Amino acids; Antibiotics; Natural products; Peptides; Polyketides

Indexed keywords

AMINO ACID; GALANTINIC ACID; NATURAL PRODUCT; POLYKETIDE; POLYPEPTIDE ANTIBIOTIC AGENT; SERINE; UNCLASSIFIED DRUG;

ARTICLE; CLAISEN CONDENSATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; REDUCTION; STEREOCHEMISTRY;

EID: 33745726063     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-941602     Document Type: Article

References (25)

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25. Ref. 5d describes the synthesis of protected galantinic butyl ester in eight steps from a commercially available serine derivative. We found that the deprotection of this butyl ester under basic conditions results in partial decomposition, epimerization, lactone formation and dehydration. The use of an acid-labile protecting group such as in the route presented in this letter thus greatly facilitates deprotection and thus the preparation of target galantinic acid.