Thiazole Aldehyde Synthesis

This review collects a part of the results of work on the thiazole-aldehyde synthesis that has been carried out over several years by various individuals whose names are reported in the references. One of us (A.D.) would like to express to all of them his gratitude and appreciation for their contribution. Financial support came from the Progetto Finalizzato Chitnica Fine e Secondaria n. 2 (Rome), the Consiglio Nazionale delle Ricerche (CNR, Rome), the Ministero della University e della Ricerca Scientifica (MURST, Rome). One of us (A. M.) is grateful to the University of Ferrara for having been appointed as Lecturer in Organic Chemistry at the Faculty of Engineering. 

Thiazole-aldehyde synthesis Preparation of aldehydes from C-2 substituted thiazoles by thiazolyl-to-formyl conversion, see A. Dondoni, Carbohydrate synthesis via thiazoles, in Modem Synthetic Methods, R. Scheffold, ed., Verlag Helvetica Chimica Acta, Basel, 1992, p. 377 A. Dondoni, Acyclic diastereoselective synthesis using functionalized thiazoles. Routes to carbohydrates and related natural products, in New Aspects of Organic Chemistry, Z. Yoshida and Y. Ohshiro, eds., Kodansha, Tokyo, and VCH, Weinhcim, 1992, p. 105. 

Dondoni et al. prepared a 1-hydroxyethylene peptide using a thiazole-aldehyde synthesis starting from an amino acid.[38] The aldehyde is converted into an alkanoate by Wittig alkenation and reduction of the double bond (Scheme 18). Then, removal of the tert-bu-tyldimethylsilyl group gives the unsubstituted lactone. In the last step, the lactone is alkylated using the method reported by Kleinman and co-workers. 20 ... 

Dondoni, A, Perrone, D, Total synthesis of (+)-galactostatin. An illustration of the utility of the thiazole-aldehyde synthesis, J. Org. Chem., 60, 4749-4754, 1995. 

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