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Usage

InChI:InChI=1/C15H24O2/c1-11(2)6-5-9-15(4,17)13-8-7-12(3)10-14(13)16/h6,10,13,17H,5,7-9H2,1-4H3/t13-,15+/m1/s1

Upstream product

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• 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 
• 129436-54-0 Diethyl-carbamic acid (1S,6R)-6-acetyl-3-methyl-cyclohex-2-enyl ester 
• 129436-55-1 Diethyl-carbamic acid (1S,6R)-6-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-3-methyl-cyclohex-2-enyl ester 
• 106144-99-4 (R)-4-(1-Hydroxy-1,5-dimethyl-hex-4-enyl)-1-methyl-cyclohex-2-enol 
• 106144-99-4 (1'R,4'S)-2-(4'-hydroxy-4'-methyl-2'-cyclohexenyl)-6-methyl-5-hepten-2-ol 
• 464892-42-0 (6S,1'S)-6-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-3-methyl-2-cyclohexenone 
• 7786-67-6 isopulegol 
• 103615-39-0 (1R,2R,5R)-5-methyl-2-((S)-2-methyloxiran-2-yl)cyclohexanol 
• 464892-40-8 (2S,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanone 
• 464892-38-4 (1R,2R,5R,1'S)-2-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-5-methylcyclohexanol 
• 465532-29-0 (2S,5R,1'S)-2-(1',5'-dimethyl-1'-trimethylsilyloxy-4'-hexenyl)-5-methylcyclohexanone 

Relevant academic research and scientific papers

Enantiospecific synthesis of (+)-hernandulcin

The sesquiterpene (+)-hernandulcin has been enantiospecifically synthesized starting from (-)-neoisopulegol in seven steps and in 25% overall yield.

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.