Galantinic Acid Research Articles

Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization

The stereoselective total synthesis of (−)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.

Preparation of Chiral Contiguous Epoxyaziridines and Their Regioselective Ring-Opening for Drug Syntheses.

Synthetically valuable chiral (aziridin-2-yl)oxirane-3-carbaldehydes bearing three consecutive functional groups including aziridine, epoxide, and aldehyde were prepared from the stereoselective epoxidation of (aziridin-2-yl)acrylaldehydes with H2 O2 using organocatalyst (2R)- or (2S)-[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as organocatalyst. The regioselective ring opening of aziridines and epoxides enabled us to achieve the highly efficient asymmetric synthesis of the antibiotic edeine D fragment 3-hydroxy-4,5-diaminopenatanoic acid, an intermediate for the formal synthesis of non-proteinogenic amino acid (-)-galantinic acid, and for potent antifungal agent (+)-preussin, and the medicinally important framework 3-hydroxy-2-hydroxymethylpyrrolidine.

Formal Synthesis of Galantinic Acid by Oxo‐Diels–Alder Methodology

AbstractThis communication presents a simple and efficient enantioselective route to galantinic acid. The strategy is based on a highly enantioselective hetero‐Diels–Alder (HDA) reaction of 3‐(4‐methoxybenzyloxy)propanal with Danishefsky's diene followed by selective introduction of further stereogenic centers thanks to the rigidity of the dihydropyran ring. The key HDA reaction is catalyzed by a new salen CrIII complex bearing a 1,1‐diphenylethyl substituent at the 3‐position of the salicyliden moiety.

Synthesis of (−)-galantinic acid via iterative hydrolytic kinetic resolution and tethered aminohydroxylation

A new synthetic strategy for (−)-galantinic acid is reported using iterative hydrolytic kinetic resolution and tethered aminohydroxylation as the key steps.

A simple entry into 1,3-diols from ( R)-2,3-cyclohexylideneglyceraldehyde: synthesis of (−)-galantinic acid

Aldehydes 5, 7, and 9 derived from easily accessible ( R)-2,3-cyclohexylideneglyceraldehyde 1 were used as novel substrates to obtain both syn- and anti-1,3-diols in several individual reactions by subjecting each of them to some practically viable metal-mediated Barbier-type allylations under moist conditions. In this regard, a detailed investigation was made regarding the compatibility and stereoselectivity associated with four such metal-mediated allylations of these aldehydes 5–7. Good yields with moderate selectivity in several successful reactions with easy chromatographic separation of diastereoisomers of the products have been elegantly exploited to isolate two pairs of enantiomerically pure syn-1,3 and anti-1,3-diols ( 6a and 6b; 10a and 10b) in substantial amounts. Finally, 10b has been exploited to synthesize (−)-galantinic acid A.

Stereoselective Total Syntheses of Leiocarpin A and (-)-Galantinic Acid Starting­ from d-Mannitol

Stereoselective total syntheses of leiocarpin A and (-)-galantinic acid, starting from D-mannitol as a chiral synthon, are described. The key steps involve stereoselective allylations, a Grignard reaction to control the required stereogenic centers, and ring-closing metathesis followed by intramolecular Michael addition.

Stereoselective Total Synthesis of (-)-Galantinic Acid

A concise, practical and stereoselective total synthesis of galantinic acid, constituent of the peptide antibiotic galantin, is reported. The title compound is obtained in six steps via Heathcock-Claisen condensation, Evans reduction and deprotection in 10% overall yield from protected serine. The route described herein thus constitutes the shortest and most efficient procedure for the preparation of the title compound disclosed so far.

Enantioselective Synthesis of (‐)‐Galantinic Acid.

Abstract An efficient enantioselective synthesis of (−)-galantinic acid 1 , a non-proteogenic amino acid is described using Sharpless asymmetric epoxidation, dihydroxylation and the regioselective nucleophilic opening of a cyclic sulfite as the key steps.

Enantioselective synthesis of (−)-galantinic acid

An efficient enantioselective synthesis of (−)-galantinic acid 1, a non-proteogenic amino acid is described using Sharpless asymmetric epoxidation, dihydroxylation and the regioselective nucleophilic opening of a cyclic sulfite as the key steps.

The sulfinyl moiety as an internal nucleophile. 2. Stereoselective synthesis of (-)-galantinic acid via 1,3-asymmetric induction.

A stereoselective synthesis of (-)-galantinic acid is disclosed. The key steps include hydrolytic kinetic resolution of a racemic epoxide and regio- and stereoselective heterofunctionalization of an olefin, using a pendant sulfinyl group as the nucleophile. The participation of the sulfinyl group was unambiguously proven by conducting the reaction in the presence of H(2)(18)O.

A straightforward enantiospecific synthesis of N-( Z)-galantinic butyl ester

A short and efficient access to the naturally occurring amino acid galantinic acid is reported using two highly diastereoselective reactions, namely a vinylogous Mukaiyama reaction and a 1,3-hydroxy directed Evans reduction.

Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of galantin I. Acid-catalyzed cyclization of galantinic acidNaomi Sakai and Yasufumi OhfuneCite this: J. Am. Chem. Soc. 1992, 114, 3, 998–1010Publication Date (Print):January 1, 1992Publication History Published online1 May 2002Published inissue 1 January 1992https://doi.org/10.1021/ja00029a031RIGHTS & PERMISSIONSArticle Views1568Altmetric-Citations58LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (2 MB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

ChemInform Abstract: Synthesis of (‐)‐Galantinic Acid from D‐Ribonolactone.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of (—)-Galantinic Acid from D-Ribonolactone

The synthesis of the revised structure of (−)-galantinic acid was achieved from D-ribonolactone

ChemInform Abstract: A New Synthetic Approach to (+)‐Galantinic Acid, Degradation Product from the Peptide Antibiotic Galantin I, via 4‐Amino‐3‐hydroxypyranose.

AbstractPhoto‐induced allylation of the protected (phenylthio)oxazolidone (I) yields the allyl derivative (III) which is converted into N‐Boc galantinic acid methyl ester (IV).

Efficient synthesis of the revised structure of (−)-galantinic acid.

The synthesis of the revised structure of galantinic acid was accomplished starting from the serinal derivative 4 via a stereoselective epoxidation of hydroxymethyl- Z-allyl amine 5 and δ-substituted- α, β-unsaturated- δ-lactone 9.

A New Synthetic Approach to (+)-Galantinic Acid, Degradation Product from the Peptide Antibiotic Galantin I, via 4-Amino-3-hydroxypyranose

5-Phenylthiooxazolidin-2-ones, derived from L-serine, were subjected to photo-induced radical allylation to give the corresponding 4-substituted 4,5-trans-5-allyloxazolidin-2-ones. 4-Ethoxyethyl derivative was led to N-Boc galant galantinic acid methyl ester via N-Boc 4-amino-3-hydroxypyranose

Total synthesis of (+)-galantinic acid

N,O-Protected L -serinal (5) afforded with diene 4, pyrone 3 as a single product which was transformed into (+)-galantinic acid derivative 8.

生理活性新規アミノ酸類の合成

Synthetic studies on biologically active and structurally unique unusual amino acids, isolated as a free form or a constituent of peptides, have been described. (1) The synthesis of neurotoxin, (-) -domoic acid (3) was achieved starting from L-glutamic acid via a stereospecific [4 + 2] cycloaddition of 5 followed by a construction of the C-1' side chain. (2) Optically pure 2-amino-3-butenol (15), prepared from L-or D-methionine, was used as the chiral serine equivalent as well as a building block for the syntesis of β-hydroxy-α-amino acid system. This was converted to the aspergillomarasmine A skeleton 24 and galantinic acid (28). (3) Significant 1, 2- and 1, 3-asymmetric induction of 2-amino-4-pentenoic acid system 17 (allylglycine) has been observed during the introduction of a hydroxyl group into its unsaturated side chain. For example, allylic oxidation of 35 provided the threo-β-hydroxyallylglycine derivative 36 as the major product, and halolactonization of 61 afforded the cis bromolactone 62, predominantly. These intermediates were efficiently transformed to the hydroxyproline analogues 40, 71, and 72. On the other hand, cyclopropylglycines (58) and (59) have been synthesized from the β-hydroxy-allylglycine derivative via a Pd (II) catalyzed [3, 3] sigmatropic rearrangement and a subsequent cyclopropanation. In addition, several useful transformations concerning amino protecting groups were also disclosed.

ChemInform Abstract: STRUCTURAL AND STEREOCHEMICAL STUDY OF GALANTINIC ACID, A NEW AMINO ACID FROM PEPTIDE ANTIBIOTIC GALANTIN I

A new amino acid, galantinic acid, was found as one of the constituent amino acids in a peptide antibiotic galantin I. The structure of galantinic acid was determined to be (2S,4S,5S)-5-amino-2-carboxymethyl-4-hydroxytetrahydropyran on the basis of NMR and CD studies.