84453-40-7

Upstream product

• 383877-46-1 (R)-2-Methyl-5-(2-methyl-oxiranyl)-cyclohex-2-enol 
• 99-48-9 (4R,6R)-carveol 
• 294634-40-5 (5R)-2-methyl-5-(2-methyloxiran-2-yl)cyclohex-2-en-1-one 
• 6485-40-1 (R)-Carvone 
• 1315381-33-9 tert-butyl{[(1R,5R,7RS)-4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl]methoxy}dimethylsilane 
• 7632-16-8 (2S,4S)-carveol 
• 383877-48-3 (5R)-2-methyl-5-(2-methyloxiran-2-yl)-1-[(trimethylsilyl)oxy]cyclohex-2-ene 
• 477841-67-1 (1R,5R,2'RS)-2-methyl-5-(2-methyloxiran-2-yl)cyclohex-2-en-1-ol 

Relevant academic research and scientific papers

Solid acid-catalysed isomerization of R(+)-limonene diepoxides

The isomerization of diastereomeric R(+)-limonene diepoxides on solid catalysts, such as clays, zeolites, and solid superacids, results in the formation of bicyclic and tricyclic oxygen-containing compounds.

Oxidation of (1S,5R,7R,S)-(4,7-Dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate

The oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7- yl)methanol epimeric at the C7 atom resulted in scalemic (5R)-5-acetyl-2- methylcyclohex-2-en-1-one. Pleiades Publishing, Ltd., 2011.

Syntheses of a prenylbisabolane diterpene, a natural insecticide from Croton linearis, and of the bisabolane sesquiterpenes (-)-delobanone and (-)-epi-delobanone

An enantioselective first total synthesis of a constituent of Croton linearis, the (-)-7-hydroxy-3,10-prenylbisaboladien-2-one 1, is described as well as the syntheses of the 7-hydroxy-3,10-bisaboladien-2-ones (-)-epi-delobanone (14a) and (-)-delobanone (14b). The model compounds, 7-hydroxy-11-nor-methyl-3-bisabolen-2-one (8a), and 11,15-nor-dimethyl-7-hydroxy-3-bisabolen-2-one (8b), were successfully prepared by opening of the protected carvone epoxide derivative 6 with the appropriate organocuprates. An alternative approach was used for compounds 1 and 14. Thus, these were obtained from homogeranyllithium or homoprenyl Grignard reagent, which reacted successfully with a masked nor-carvone, ketone 11, prepared in four steps from (R)-carvone.

Bottrospicatols, Novel Monoterpenes Produced on Conversion of (-)- and (+)-cis-Carveol by Streptomyces

The conversion of (-)-cis-carveol and (+)-cis carveol by Streptomyces bottropensis SY-2-1 and S. ikutamanensis Ya-2-1 was investigated.S. bottropensis SY-2-1 transformed (-)-cis-carveol mainly to (+)-bottrospicatol (1), with (+)-isobottrospicatol (2) as one of the minor products.On the other hand, strain SY-2-1 transformed (+)-cis-carveol mainly to (-)-isobottrospicatol (4), with (-)-bottrospicatol (3) as one of the minor products.S. ikutamanensis Ya-2-1 metabolized the cis-carveols in the same way into bottrospicatols.The metabolic pathways for (-)-cis-carveol and (+)-cis-carveol in S. bottropensis SY-2-1 and S. ikutamanensis Ya-2-1, and the biological activities of bottrospicatols are described in this paper.