106145-00-0

Upstream product

• 110-93-0 6-Methyl-hept-5-en-2-on 
• 54781-27-0 4-methyl-2-trimethylsilyloxycyclohexa-1,3-diene 
• 106882-17-1 (1S,6R)-6-((S)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-3-methyl-cyclohex-2-enol 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 
• 96-08-2 R-(+)-limonene diepoxide 
• 106144-98-3 (R)-4-(1-Hydroxy-1,5-dimethyl-hex-4-enyl)-1-methyl-2-phenylselanyl-cyclohexanol 
• 106144-98-3 (1S,2S,4R)-4-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-1-methyl-2-phenylselenocyclohexanol 
• 96-08-2 (4R)-(+)-1,2,8,9-diepoxy-p-menthane 
• 106144-97-2 (1'R)-6-methyl-2-(3',4'-epoxy-4'-methylcyclohexyl)-5-hepten-2-ol 
• 5989-27-5 D-limonene 
• 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 

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.

O-1-(1,3-butadienyl) carbamates as diels-alder dienes: Stereospecific synthesis of (±)-Hernandulcin and congeners

The TiCl4-catalyzed addition of the title reactants to vinyl ketones regio- and stereospecifically yields cis-disubs, cyclohexenes which add RMgX stereospecifically to the ketone. A final product in this sequence is the intensely sweet sesquiterpene, hernandulcin.

Synthesis of (+/-)-Hernandulcin by an Intramolecular Nitrile Oxide Cycloaddition Route from Farnesol

An intramolecular addition reaction of the nitrile oxide derived from (2Z,6E)-farnesal oxime afforded an isoxazoline derivative, which was converted into hernandulcin, a sweet sesquiterpene of Verbenaceae plant.

SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-HERNANDULCIN. A NEW SESQUITERPENE WITH INTENSELY SWEET TASTE

The absolute configuration of (+)-hernandulcin was shown to be 6S,1'S by synthesizing it from (R)-(+)-limonene.

SYNTHESIS OF (6S,1'S)-(+)-HERNANDULCIN, A SWEETNER, AND ITS STEREOISOMERS

All of the four possible stereoisomers of hernandulcin were synthesized starting from the enantiomers of limonene.The absolute configuration of the naturally occuring and sweet-tasting (+)-hernandulcin was established as 6S,1'S.Other stereoisomers were not sweet at all.