Olefin Metathesis in Carbohydrate Chemistry

Authors: Jorgensen M.; Hadwiger P.; Madsen R.; Stutz A.E.; Wrodnigg T.M.

Source: Current Organic Chemistry, Volume 4, Number 6, June 2000 , pp. 565-588(24)

Publisher: Bentham Science Publishers

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Abstract:

This account is devoted to a discussion of synthetic applications of olefin metathesis in carbohydrate chemistry.

Olefin metathesis has emerged as a highly promising and exciting area in the contemporary organic synthesis of carbon-carbon bonds. Metathetic ring-closure (RCM) of diene precursors is advancing into one of the most useful and frequently applied transformations in modern organic chemistry. The development has been particularly rapid in recent years following the introduction of efficient transition metal carbene catalysts as reflected by the number of reviews on the general field of olefin metathesis in recent years.

Cross-metathesis of suitably functionalized carbohydrates with well-defined metal carbene complexes is yet another of the big promises in carbohydrate synthesis for years to come. Compared with the ring-closing metathesis, this variation of the theme has, to date, received much less attention from the scientific community despite the fact that it has proved to be of tremendous synthetic value in the area of organometallic chemistry.

Keywords: Olefin Metathesis; Carbohydrate chemistry; Metathetic ring closure; Ring closing; Synthesis; Carbocycles; Five membrane carbocycles; Heterocycles; Oxacycles; Azacycles; Complex natural products; Cross metathesis; Homodimerisation