403483-78-3Relevant articles and documents
A novel extension of the Stork-Jung vinylsilane Robinson annelation procedure for the introduction of the cyclohexene of guanacastepene
Snider, Barry B,Shi, Bo
, p. 9123 - 9126 (2001)
A new annelation procedure has been developed in a model system to introduce the cyclohexene ring of guanacastepene. Cyclohexenone 16 is prepared by sequential methylation and alkylation with allylic iodide 15. One-pot epoxidation, protodesilylation and hydrolysis of the THP forms dione 19, which cyclizes with NaOMe to 24 in 57% overall yield. Reduction, Mitsunobu inversion, and selective oxidation of the primary alcohol forms model 29. Phenyldimethylsilyl allylic iodide 36 is easier to make and more stable than trimethylsilyl allylic iodide 6 used by Stork.
NOVEL CYCLIC OXYGENATED COMPOUNDS HAVING COOLING, FRAGRANCE, AND FLAVOR PROPERTIES, AND USES THEREOF
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Page/Page column 15, (2008/06/13)
Compositions that include compounds capable of producing a cooling sensory effect such as certain hydroxy-ketones and hydroxy-aldehyde compounds, their cyclic semi-ketals and semiacetals, and other derivatives thereof. The compounds impart a refreshing and cooling sensation of long duration and high potency, and thus are useful in a variety of formulations, including consumer products such as mouth formulations, food and beverage products, tobacco and smoking articles, fragrances, toiletries, oinments, and the like.
