Metal Carbenes in Natural Product Synthesis

Abstract

A study of the application of rhodium stabilised carbene intermediates in the preparation of furofuran lignans, products of biosynthesis in all lignin containing plants, resulted in the development of a new strategy for the synthesis of these compounds. After the successful preparation of a model series of compounds proved the viability of the process it was applied to the synthesis of (±)-epimagnolin A, a non-symmetrical furofuran lignan, was prepared by total synthesis for the first time.

En route to the target compounds an efficient method for the preparation of electron rich, aromatic substituted cyclobutanones and a reliable way of preparing α-diazo-γ-butyrolactones were each investigated. In both cases the results suggest that the methodology might well find a more general role in organic synthesis.

A more brief investigation into a new synthetic route towards laurencin, a medium ring ether of marine origin, failed to produce convincing results. The preparation of the substrates for the pivotal ruthenium(II) catalysed metathesis reaction proved difficult to the extent that a wide survey of the catalysts available for ring closing metathesis was not possible. Nonetheless, the preparation of suitable 1,2,4-triols was ultimately achieved and future investigations in this area will be facilitated by the early results described herein.

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