Chapter 13 Rauwolfia Alkaloids with Special Reference to the Chemistry of Reserpine1

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This chapter describes Rauwolfia alkaloids with special reference to the chemistry of reserpine. Rauwolfia products have become important therapeutic agents, both as sedatives and antihypertensives. Although their production and use have fallen off since the peak years of 1955 and 1956, it is estimated that their total sales a t the consumers' level in 1961 still amounted to $100 million in the United States alone. Since 1952, the year reserpine was first isolated, several thousand articles have been published on the isolation, chemistry, pharmacology, and clinical aspects of reserpine and other Rauwolfia alkaloids, and today these investigations are still being pursued. Botanists estimate the number of identified Rauwolfia species to be about 50, of which R. serpentina, R. canescens, R. vomitoria, and R. ligustrina have been investigated in detail. Only the first three species are important from the standpoint of supplies of therapeutically useful alkaloids; the last species is not especially rich in reserpine, but has nevertheless been investigated in great detail. The Indian plant, R. serpentina, has lost much of its importance (except for local production), as its reserpine content (0.1%) is only about half that of R. vomitoria, which is at present the most important species. It grows so plentifully in Central Africa, especially in the Congo, that cultivation is not necessary. It is considerably taller than R. serpentina, and procedures have been developed by Congolese collectors by which the smaller side roots may be cut periodically without loss of the tree.

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    • Chemical and Biological Perspectives of Monoterpene Indole Alkaloids From Rauwolfia species

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      Due to the outstanding pharmacological profile of Rauwolfia species, medicinal chemists have paid particular attention and given considerable effort to the synthesis of complex MIAs. During the past 50 years, the design and synthesis of pharmacologically active Rauwolfia species has been achieved by many synthetic chemists [106–111]. This part of the chapter focuses on the total synthesis of the most popular MIAs.

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    1

    For the most recent review of chemistry and pharmacology of the Rauwolfia alkaloids see R. A. Lucas in ‘Progress in Medicinal Chemistry” (G. P. Ellis and G. B. West, eds.), p. 146. Butterworths, Washington and London, 1963.

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