97335-22-3

Upstream product

• 471861-81-1 (1R,3S,4S,5S,7R,9R,10R,11R)-1,9-diacetyloxy-7-p-nitrobenzoyloxylongipinane 

Downstream Products

• 471861-88-8 (1R,3S,4S,5S,7R,9R,10R,11R)-1,7-diacetyloxy-9-p-nitrobenzoyloxylongipinane 
• 471861-81-1 (1R,3S,4S,5S,7R,9R,10R,11R)-1,9-diacetyloxy-7-p-nitrobenzoyloxylongipinane 
• 471861-78-6 (1R,3S,4S,5S,7R,9R,10R,11R)-1,9-dihydroxy-7-p-nitrobenzoyloxylongipinane 
• 471861-79-7 (1R,3S,4S,5S,7R,9R,10R,11R)-1,7-dihydroxy-9-p-nitrobenzoyloxylongipinane 

Relevant academic research and scientific papers

Quirogane, prenopsane, and patzcuarane skeletons obtained by photochemically induced molecular rearrangements of longipinene derivatives

Ultraviolet irradiation of (1R,3S,4S,5S,10R,11R)-1-acetyloxy-7-oxolongipin-8-ene (6), prepared from longipinene diesters isolated from Stevia salicifolia, afforded the new quirogane (7) and prenopsane (8) derivatives, as the major products, together with the minor secondary photoproduct (1R,3R,5R,8S,11S)-1-acetyloxy-7-oxopatzcuar-9-ene (9), which possesses a novel tricyclic sesquiterpene skeleton. The stereostructures of the new compounds 7-9 were mainly determined by NMR techniques including COSY, HSQC, HMBC, and NOESY in combination with molecular modeling obtained by density functional theory calculations. A reaction mechanism accounting for the observed transformations is proposed.