477841-82-0

Upstream product

• 383877-46-1 (R)-2-Methyl-5-(2-methyl-oxiranyl)-cyclohex-2-enol 
• 294634-40-5 (5R)-2-methyl-5-(2-methyloxiran-2-yl)cyclohex-2-en-1-one 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 477841-80-8 (6R)-2-[(tert-butyldiphenylsilyl)oxy]-7-hydroxy-10-prenyl-7,8-dihydro-α-bisabolene 

Relevant academic research and scientific papers

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.