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Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof (Articolo in rivista)

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Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof (Articolo in rivista) (literal)

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Rassu G., Auzzas L., Pinna L., Zambrano V., Zanardi F., Battistini L., Marzocchi L., Acquotti D., Casiraghi G. (2002)
Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof
in Journal of organic chemistry
(literal)

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Rassu G., Auzzas L., Pinna L., Zambrano V., Zanardi F., Battistini L., Marzocchi L., Acquotti D., Casiraghi G. (literal)

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La rivista è al primo posto per numero totale di citazioni (63233 citazioni totali) nella categoria ISI ¡V Chimica Organica. La stessa è al terzo posto tra le 12 riviste più richieste dell¡¦area chimica (CAS Science Spotlight). (literal)

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A highly efficient, ¡§chiral-pool¡¨ synthetic grid delivering preparatively useful yields of amino alcohols 1-4 and amino acids 5-8 has been established. As foreseen in the retrosynthetic analysis of Scheme 1, the carbasugar products were assembled by conjoining two readily accessible substructures, TBSOP 9 (ex pyrrole), and glyceraldehyde 10 (ex D-mannitol). The pathways are highlighted by three key transformations: (1) a crossed vinylogous Mukaiyama-type aldolization to install the first carbon-carbon juncture between 9 and 10; (2) a novel silylative cycloaldolization10 to implement the second carbon-carbon linkage and complete the construction of the desired cyclopentanoid and cyclohexanoid structures; (3) a reductive or hydrolytic cleavage of the lactam tether which liberates both the amino and the hydroxymethyl or carboxyl functionalities within the cyclitol frames. This approach, whose scope could be enlarged to include aldehyde acceptors other than D-glyceraldehyde, enabled us to provide preparatively useful quantities of enantiopure amino alcohol or amino acid entities with which many diverse, oxygen-decorated oligomeric architectures may be assembled. (literal)

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Istituto di Chimica Biomolecolare del CNR, Sezione di Sassari, Traversa La Crucca 3, Regione Baldinca, I-07040 Li Punti, Sassari, Italy, Dipartimento di Chimica, Università di Sassari, Via Vienna 2, I-07100 Sassari, Italy, Dipartimento Farmaceutico, Università di Parma, Parco Area delle Scienze 27A, I-43100 Parma, Italy, Centro Interfacoltà di Misure ¡§G. Casnati¡¨, Università di Parma, Parco Area delle Scienze 23A, I-43100 Parma, Italy (literal)

Titolo

Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof (literal)

Abstract

A chiral, divergent synthesis of two carbafuranosylamines, 1 and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-Ë(tert-butyldimethylsilyl)oxyÍpyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high yielding silylative cyclo-aldolization which gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)¡VN link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12 and 13 step processes, with overall yields of 34%, 35%, 17% and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields. (literal)

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