144831-70-9

Upstream product

• 108-05-4 vinyl acetate 
• 58461-27-1 (+/-)-lavandulol 
• 7086-79-5 (3S)-4-methyl-3-(3-oxobutyl)pent-4-enal 
• 7086-79-5 (R)-4-methyl-3-(3'-oxobutyl)pent-4-enal 
• 1327155-01-0 C₁₂H₂₂O₂ 
• 1327155-06-5 C₁₂H₂₂O₂ 
• 1327155-00-9 (5R)-5-isopropenyl-2-methyl-octane-2,7-diol 
• 1327155-05-4 (5S)-5-isopropenyl-2-methyl-octane-2,7-diol 
• 1345866-28-5 C₁₂H₂₂O₃ 
• 1327155-03-2 (S)-2-isopropenyl-5-methyl-hexane-1,5-diol 
• 869162-67-4 (5S)-6-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone 
• 1298063-04-3 (2E,5S)-2-methyl-5-(prop-1-en-2-yl)hex-2-enedial 
• 869168-74-1 (6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 
• 1298063-18-9 (2E,5S)-2-methyl-5-(prop-1-en-2-yl)hex-2-ene-1,6-diyl diacetate 

Downstream Products

• 50373-53-0 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 

Relevant academic research and scientific papers

Enzymatic transesterification of racemic lavandulol: Preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate

(R) and (S)-lavandulol are important compounds in the cosmetics industry and in pheromone research. The senecioyl ester of (S)-lavandulyl has recently been identified as the sex pheromone of the vine mealybug, a significant pest in vineyards. We herein report the preparation of the two enantiomers of lavandulol and lavandulyl senecioate, starting from racemic lavandulol. The preparation is based on a two-cycle enzymatic transesterification of racemic lavandulol with vinyl acetate using Porcine pancreas lipase. High enantioselectivity was achieved while the preparation yielded (R)-lavandulol with 96.7% ee and (S)-lavandulol with 92.6% ee.

Chemomicrobial synthesis of (R)- and (S)-lavandulol

(R)- and (S)-Lavandulol are important compounds in the cosmetics industry and in pheromone research. We have developed syntheses of (R)- and (S)-lavandulol from (S)- and (R)-limonene, respectively, by microbial Baeyer-Villiger oxidation of the intermediate unsaturated hydroxy ketone. It has been found that the same strain of Acremonium roseum can be successfully used in the key step of the synthesis of both enantiomers of lavandulol.

Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol

Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.

Grob-type fragmentation of a carvone derived β-hydroxymesylate: Application to the synthesis of chiral lavandulol derivatives

Grob-type fragmentation of the carvone derived diol-monosulphonate 5 has been utilised for the enantioselective synthesis of various lavandulol derivatives