110715-84-9

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 
• 5989-54-8 (-)-(S)-limonene 
• 106144-97-2 (1'S)-6-methyl-2-(3',4'-epoxy-4'-methylcyclohexyl)-5-hepten-2-ol 
• 106144-98-3 (1R,2R,4S)-4-(1'-hydroxy-1',5'-dimethyl-4'-hexenyl)-1-methyl-2-phenylselenocyclohexanol 
• 96-08-2 (4S)-(-)-1,2,8,9-diepoxy-p-menthane 
• 106144-99-4 (1'S,4'R)-2-(4'-hydroxy-4'-methyl-2'-cyclohexenyl)-6-methyl-5-hepten-2-ol 
• 129436-55-1 Diethyl-carbamic acid (1S,6R)-6-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-3-methyl-cyclohex-2-enyl ester 
• 129436-54-0 Diethyl-carbamic acid (1S,6R)-6-acetyl-3-methyl-cyclohex-2-enyl ester 
• 37586-57-5 4-methyl-3-pentenylmagnesium bromide 

Relevant academic research and scientific papers

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.

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 (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.