38978-06-2

Usage

Chemical class

Gona-dien-3-one derivatives

Type of compound

Synthetic organic compound

Structural features

Steroid-like compound
Two methyl groups at the 10th and 17th positions

Applications

Research and pharmaceutical industries
Precursor in the synthesis of various pharmaceuticals and hormone-related compounds

Potential uses

Development of drugs for hormonal disorders
Reproductive health
Related medical conditions

Importance in production

Vital intermediate in the production of steroidal drugs
Hormonal preparations for medical use
These properties and specific content provide a comprehensive overview of 10,17-dimethylgona-4,13(17)-dien-3-one, highlighting its chemical structure, applications, and significance in the pharmaceutical and medical fields.

Upstream product

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Relevant academic research and scientific papers

2-(Prenyloxymethyl)benzoyl (POMB) group: a new temporary protecting group removable by intramolecular cyclization

2-(Prenyloxymethyl)benzoates can be prepared from alcohols and readily available 2-(prenyloxymethyl)benzoic acid by standard acylation techniques or by Mitsunobu reaction with inversion of configuration. The POMB group can be cleaved first by oxidative removal of the prenyl group with DDQ followed by lactonization with expulsion of the alcohol catalyzed by Yb(OTf)3. These reaction conditions are compatible with the presence of a large number of common protecting groups.

Chloromethanesulfonate as an efficient leaving group: Rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles

The chloromethanesulfonate (monochlate) served as an efficient leaving group for rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles. The treatment of the monochlate 16a with zinc acetate in dioxane at 90 °C effected migration of the 4α-methyl group to give alkene 17a. Upon similar treatment of the monochlates 22a, 25a, 28a, and 31a with zinc acetate, the carbon-carbon bonds antiperiplanar to the hydroxyl groups efficiently migrated to afford the alkenes 23a, 26a-c, 29a,b, and 32a, respectively. In the case of the diol 40, the monochlate was converted into the ketone 41 via a rearrangement-ring expansion. The reaction of the monochlates 44a, 47a, 49a, 52a, and 57a with sodium azide or lithium azide in N,N-dimethylformamide efficiently afforded the azides with inversion of the configuration. The introduction of a nitrile group to the sterically hindered alcohol 59 was performed in high yield by the reaction of the monochlate 60a with sodium cyanide.