Add to ORKGWe describe the stereoselective transformation of diosgenin () to (25R)-Delta(4)-dafachronic acid (), (25R)-Delta(7)-dafachronic acid (), and (25R)-cholestenoic acid (), which represent potential ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans. Key-steps of our synthetic approach are a modified Clemmensen reduction of diosgenin () and a double bond shift from the 5,6- to the 7,8-position. In the 25R-series, the Delta(7)-dafachronic acid exhibits the highest hormonal activity
27-Nor-Δ4-dafachronic acid was prepared in nine steps and 14% overall yield by two sequential 2-carb...
SummaryC. elegans diapause, gonadal outgrowth, and life span are regulated by a lipophilic hormone, ...
Endogenous small molecule metabolites that regulate animal longevity are emerging as a novel means t...
We describe the stereoselective transformation of diosgenin () to (25R)-Delta(4)-dafachronic acid ()...
We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ...
Using a highly stereoselective Evans aldol reaction for the introduction of the stereogenic center a...
Synthesis and testing of dafachronic acid A ( 1) and its derivatives 2 and 3 have revealed that 1, a...
SummaryIn response to environmental and dietary cues, the C. elegans orphan nuclear receptor, DAF-12...
In response to environmental and dietary cues, the C. elegans orphan nuclear receptor, DAF-12, regul...
Cholesterol-derived hormones, the dafachronic acids, play a major role in controlling the life cycle...
Dafachronic acids (DAs) are 3-keto cholestenoic acids bearing a carboxylic acid moiety at the end of...
Cholesterol is essential for the survival of the nematode Caenorhabditis elegans. Recent studies hav...
The development and lifespan of C. elegans are controlled by the nuclear hormone receptor DAF-12, an...
Larvae of the nematode Caenorhabditis elegans must choose between reproductive development and dauer...
The development and lifespan of C. elegans are controlled by the nuclear hormone receptor DAF-12, an...
27-Nor-Δ4-dafachronic acid was prepared in nine steps and 14% overall yield by two sequential 2-carb...
SummaryC. elegans diapause, gonadal outgrowth, and life span are regulated by a lipophilic hormone, ...
Endogenous small molecule metabolites that regulate animal longevity are emerging as a novel means t...
We describe the stereoselective transformation of diosgenin () to (25R)-Delta(4)-dafachronic acid ()...
We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ...
Using a highly stereoselective Evans aldol reaction for the introduction of the stereogenic center a...
Synthesis and testing of dafachronic acid A ( 1) and its derivatives 2 and 3 have revealed that 1, a...
SummaryIn response to environmental and dietary cues, the C. elegans orphan nuclear receptor, DAF-12...
In response to environmental and dietary cues, the C. elegans orphan nuclear receptor, DAF-12, regul...
Cholesterol-derived hormones, the dafachronic acids, play a major role in controlling the life cycle...
Dafachronic acids (DAs) are 3-keto cholestenoic acids bearing a carboxylic acid moiety at the end of...
Cholesterol is essential for the survival of the nematode Caenorhabditis elegans. Recent studies hav...
The development and lifespan of C. elegans are controlled by the nuclear hormone receptor DAF-12, an...
Larvae of the nematode Caenorhabditis elegans must choose between reproductive development and dauer...
The development and lifespan of C. elegans are controlled by the nuclear hormone receptor DAF-12, an...
27-Nor-Δ4-dafachronic acid was prepared in nine steps and 14% overall yield by two sequential 2-carb...
SummaryC. elegans diapause, gonadal outgrowth, and life span are regulated by a lipophilic hormone, ...
Endogenous small molecule metabolites that regulate animal longevity are emerging as a novel means t...