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Lignans: Some Properties and Syntheses

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The Shikimic Acid Pathway

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 20))

Abstract

Lignans are widely distributed plant products which are dimers of phenylpropanoids derived from shikimic acid.1 Particularly common are the dimers derived from two units at the coniferyl alcohol oxidation level. Rather confusingly, the term ‘neolignan’2 has been coined to describe some dimers formally derived from the dimerisation of propenyl- and allylphenols. In fact, nothing is known of the biosynthesis of these compounds and many so-called ‘neolignans’ may well have their oxidation levels adjusted after, rather than before, dimerisation. However, many compounds, not ββ-linked, occur among ‘neolignans’ leading to a wide structural diversity which perhaps justifies the sub-grouping. The carbon skeletons of ββ-linked lignans, together with some naturally occurring rearrangement products and their most common oxidation levels (substi-tuents are almost always H, OH, OMe, OCOR) are shown in Figure 1 and these compounds are the subject of this chapter. The carbon frameworks of the ‘neolignans’ are shown in Figure 2.

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  1. Department of Chemistry, University College of Swansea, Swansea, SA2 9PP, UK

    Andrew Pelter

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  1. University of California, Davis, Davis, California, USA

    Eric E. Conn

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Pelter, A. (1986). Lignans: Some Properties and Syntheses. In: Conn, E.E. (eds) The Shikimic Acid Pathway. Recent Advances in Phytochemistry, vol 20. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-8056-6_8

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  • DOI: https://doi.org/10.1007/978-1-4684-8056-6_8

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