Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen

1955/01/01 by A. Eschenmoser, Albert Eschenmoser, L. Ruzicka +3 · 11 citations
Biochemistry, Genetics and Molecular Biology · #Plant biochemistry and biosynthesis #Natural product bioactivities and synthesis #Phytochemical compounds biological activities

paper · doi:10.1002/hlca.19550380728

Abstract

Abstract The biogenetic isoprene rule in its application to the triterpenes is discussed from a stereochemical standpoint. On the basis of a well defined system of arbitrary assumptions a scheme has been developed leading from squalene to the formulae of the basic representatives of all known cyclic triterpene groups ‐ i.e. euphol, tirucallol, lupeol, taraxasterol, germanicol, β‐amyrin, taraxerol, friedelin, α‐amyrin, lanosterol ‐ in their full structural and configurational detail. This result is considered to support the squalene hypothesis of the biogenesis of cyclic triterpenes.

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