77480-25-2

Upstream product

• 4677-48-9 Isoalantolactone 
• 77480-24-1 Acetic acid (R)-2-((2R,3R,4aR,8aS)-3-hydroxy-4a-methyl-8-methylene-decahydro-naphthalen-2-yl)-propyl ester 
• 77480-20-7 (3R,3aR,4aS,8aR,9aR)-3,8a-Dimethyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one 
• 77480-21-8 Dihydroalantolactone 
• 54911-04-5 (3aα,4aα,8aβ,9aα)-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-8a-methyl-5-methylenenaphtho<2,3-b>furan-2(3H)-one 
• 77480-23-0 (2R,4aS,8aR)-3-((R)-2-Hydroxy-1-methyl-ethyl)-8a-methyl-5-methylene-decahydro-naphthalen-2-ol 
• 77415-52-2 Acetic acid (R)-2-((4aR,8aS)-4a-methyl-8-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl)-propyl ester 

Relevant academic research and scientific papers

Stereospecific Total Synthesis of (+/-)-Vetiselinenol

(+/-)-Vetiselinenol (1) and (+/-)-11-epivetiselinenol (12) have been synthesized by stereospecific routes using methyl lactones 4 and 3 to establish the desired stereochemistry at C-11.Equilibration studies indicated that the thermodynamic mixture of the lactones 3/4 is 45:55.Reductive opening of the lactones, selective acetylation, dehydration, and hydrolysis gave 1 and 12.Both 1 and 12 were converted to (+/-)-vetiselinene (15), establishing that they were indeed C-11 epimers.