Oxidative transformations of cembrane diterpenoids IV. Photooxidation of cembrene

Nitrosochlorination of cembrene

“…Thus, addition reactions to the double bonds proceed stereoselectively to give products arising from an attack of a reagent from the outside plane of the double bond. 7 Therefore, the addition of amines to nitroso olefin 3 should proceed stereochemically similar to the addition of electrophiles to the 4,5-double bond in 1 and lead to the S-configuration of carbon in the 4-position. This reaction stereochemistry was supported by NMR spectroscopy and calculated data.…”