ArticleThe Journal of organic chemistry2014
Synthesis of a smoothened cholesterol: 18,19-di-nor-cholesterol.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 13 citations in OpenAlex.
- Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds.Beilstein journal of organic chemistry · 2025Review
- Alcohols as Efficient Intermolecular Initiators for a Highly Stereoselective Polyene Cyclisation Cascade.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Review
- Subverting Hedgehog Protein Autoprocessing by Chemical Induction of Paracatalysis.Biochemistry · 2020Article
- Multiscale Simulations of Biological Membranes: The Challenge To Understand Biological Phenomena in a Living Substance.Chemical reviews · 2019Article
- Nanoscale Membrane Domain Formation Driven by Cholesterol.Scientific reports · 2017Article
- Building Synthetic Sterols Computationally - Unlocking the Secrets of Evolution?Frontiers in bioengineering and biotechnology · 2015Review
- Eliminating the roughness in cholesterol's β-face: does it matter?Langmuir : the ACS journal of surfaces and colloids · 2014Article
Corrections and comments
- Erratum issued
Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Herein, we report the first synthesis of a demethylated form of cholesterol (18,19-di-nor-cholesterol), in which the C18 and C19 methyl groups of the β-face were eliminated. Recent molecular simulations modeling 18,19-di-nor-cholesterol have suggested that cholesterol's opposing rough β-face and smooth α-face play necessary roles in cholesterol's membrane condensing abilities and, additionally, that specific facial preferences are displayed as cholesterol interacts with different neighboring lipids and transmembrane proteins. Inspired by these poorly characterized biochemical interactions, an extensive 18-step synthesis was completed as part of a collaborative effort, wherein synthesizing a "smoothened" cholesterol analogue would provide a direct way to experimentally measure the significance of the β-face methyl groups. Starting from known perhydrochrysenone A, the synthesis of 18,19-di-nor-cholesterol was accomplished with an excellent overall yield of 3.5%. The use of the highly stereoselective Dieckmann condensation and the employment of Evans' chiral auxiliary were both key to ensuring the success of this synthesis.
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Registered trials
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