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Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen
Helvetica Chimica Acta · 1955 · Vol. 38(7) · pp. 1890–1904
Albert Eschenmoser✉(Analytisches Laboratorium)L. Růžička(Analytisches Laboratorium)O. Jeger(Analytisches Laboratorium)D. Arigoni(Analytisches Laboratorium)
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.
Plant biochemistry and biosynthesisNatural product bioactivities and synthesisPhytochemical compounds biological activitiesChemistryLupeolTriterpeneFriedelinLanosterolStereochemistrySqualeneTerpeneSterolTriterpenoid
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References
The isoprene rule and the biogenesis of terpenic compounds
Cellular and Molecular Life Sciences · 1953 · 715 citations
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