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

Eschenmoser A. | Zendy; Ruzicka L. | Zendy; Jeger O. | Zendy; Arigoni D. | Zendy

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

Author(s) -

Eschenmoser A.,

Ruzicka L.,

Jeger O.,

Arigoni D.

Publication year - 1955

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19550380728

Subject(s) - chemistry , lupeol , triterpene , friedelin , lanosterol , stereochemistry , squalene , terpene , sterol , triterpenoid , organic chemistry , biochemistry , cholesterol , medicine , alternative medicine , pathology

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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