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Expeditious synthesis of the key unnatural aminoacid in the formal asymmetric total synthesis of (-)-Jorumycin and bioactive tetrahydroisoquinoline alkaloids

Ulgheri, Fausta and Fontana, Angelo and Spanu, Pietro (2013) Expeditious synthesis of the key unnatural aminoacid in the formal asymmetric total synthesis of (-)-Jorumycin and bioactive tetrahydroisoquinoline alkaloids. In: 35. Convegno della Divisione di chimica organica della Società Chimica Italiana, 9-13 settembre 2013, Sassari, Italia. [S.l.], Società Chimica Italiana, Divisione di chimica organica. P28. Conference or Workshop Item.

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Abstract

The synthesis of the enantiopure aminoacid, key intermediate in the total synthesis of (-)-Jorumycin and of various bioactive tetraidroisoquinoline alkaloids analogues, a class of compounds with antitumor and antibiotic activities, has been accomplished starting from 2,4-dimethoxy-3-methyl-benzaldehyde 1 in only 5 steps and in a very high yield. This synthesis, based on a Negishi reaction between a 5-iodo-2,4-dimethoxy-3-methylphenol and N-(tert-Butoxycarbonyl)-3-iodo-L-alanine methyl ester, permits an easy access to the intermediate, and the formal asymmetric total synthesis of (-)-Jorumycin and tetrahydroisoquinoline alkaloids of the same family, in a very shorter way with respect to the syntheses previously reported.

Item Type:Conference or Workshop Item (Poster)
ID Code:9290
Status:Published
Uncontrolled Keywords:Jorumycin, alkaloids, synthesis
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Società Chimica Italiana, Divisione di chimica organica
Publisher Policy:Depositato per gentile concessione dell'Editore
Deposited On:05 Nov 2013 08:48

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