673451-22-4

Upstream product

• 673451-21-3 (3R,6S,1'R)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-(phenylseleno)cyclohexanone 
• 674291-00-0 (2S,5R,1'R)-2-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-5-methylcyclohexanone 
• 673451-18-8 (1R,2R,5R,1'R)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol 
• 673451-19-9 (2S,5R,1'R)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanone 
• 103615-41-4 (1R,2R,5R)-5-methyl-2-((R)-2-methyloxiran-2-yl)cyclohexan-1-ol 
• 7786-67-6 isopulegol 

Downstream Products

• 106145-00-0 (6S,1'R)-6-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-3-methyl-2-cyclohexenone 

Relevant academic research and scientific papers

A facile synthesis of (6S,1′S)-(+)-hernandulcin and (6S,1′R)-(+)-epihernandulcin

A facile total synthesis of (+)-hernandulcin (1) was accomplished from (-)-isopulegol in 6 steps with 15% overall yield. Epoxidation of (-)-isopulegol with m-chloroperbenzoic acid followed by opening of the epoxide 3a with prenyl Grignard afforded the tertiary alcohol 4a with correct C-6 and C-1′ stereochemistry as a major product. Oxidation of the secondary alcohol in compound 4a to the ketone 5a was accomplished in high yield by using TPAP and N-methylmorpholine N-oxide. Conversion of the ketone 5a to α,β -unsaturated ketone via organoselenium intermediate gave (+)-hernandulcin (1). This method was also successfully applied to the synthesis of (+)-epihernandulcin (2).

Synthesis of (+)-hernandulcin and (+)-epihernandulcin

(+)-Hernandulcin 1, an extremely sweet bisabolane-type sesquiterpene, and (+)-epihernandulcin 2 were synthesized in six steps from (-)-isopulegol with 15 and 11 percent overall yields, respectively.