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Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen
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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Citations
Cited by
Cascade Reactions in Total Synthesis
Nicolaou, K. C., Edmonds, D. J., & Bulger, P. G. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200601872 · Cited by 2,101
Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future
Tietze, L. F., & Beifuss, U. (1993) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199301313 · Cited by 1,379
On the origins of triterpenoid skeletal diversity
Xu, R., Fazio, G. C., & Matsuda, S. P. T. (2004) · Phytochemistry · doi:10.1016/j.phytochem.2003.11.014 · Cited by 567
Biogenesis, molecular regulation and function of plant isoprenoids.
Bouvier, F., Rahier, A., & Camara, B. (2005) · Progress in Lipid Research · doi:10.1016/j.plipres.2005.09.003 · Cited by 498
Studies on Squalene Epoxidase of Rat Liver
Yamamoto, S., & Bloch, K. (1970) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)77144-0 · Cited by 163
Metadata
- Authors
- Eschenmoser, A., Ruzicka, L., Jeger, O., & Arigoni, D.
- Venue
- Helvetica Chimica Acta
- Publisher
- Wiley
- Published
- 1955-01
- Volume
- 38
- Issue
- 7
- Pages
- 1890-1904
- ISSN
- 0018-019X (ISSN-L)
- 1522-2675
- OpenAlex
- W1987126722
- Cited by
- 604
- References
- 0
- FWCI
- 9.63
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. https://app.cochat.ai/papers/10.1002/hlca.19550380728
- The paper
- Eschenmoser, A., Ruzicka, L., Jeger, O., & Arigoni, D. (1955). Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. Helvetica Chimica Acta. https://doi.org/10.1002/hlca.19550380728
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
