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

A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride: simple preparation of enantiomerically pure (R)-lavandulol

“…These specific enzymes were chosen on the basis of our previous screening of different lipases for the resolution of (±)-lavandulol. 6 The conversion rate using the Hog pancreas was higher than that with the Porcine pancreas and the enantioselectivity in diethyl ether was higher than that in tert-butylmethyl ether (Table 1). In a comparative experiment using the two enzymes in ether, a conversion rate of 50% was obtained after 24 h with the Hog pancreas as compared with a 42% conversion rate after 53 h with the Porcine pancreas.…”

“…4,5 We have recently developed a two stage enzymatic separation of commercial (±)-lavandulol using vinyl acetate as the acylating reagent to provide the two enantiomers in good enantiomeric excess. 6 The drawback of this method is the need of lengthy column chromatography in order to separate the unreacted alcohol from the formed acetate. Due to our continuing interest in the lavandulol enantiomers and the recent discovery of pheromones comprising of (R)-lavandulol and its esters in different insects, we herein report a simplified enzymatic resolution of (±)-lavandulol, which avoids chromatography through the use of succinic anhydride as the acylating reagent, particularly for preparation of the (R)-enantiomer.…”

Fungal mediated kinetic resolution of racemic acetates to ( R )-alcohols using Fusarium proliferatum

“…Enzyme mediated kinetic resolution of such alcohols using lipases, esterases, and alcohol dehydrogenases have been reported in the literature. [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] For example, resolution of (±)-lavandulol has been achieved previously with various lipases such as Candida antarctica lipase B (CAL B), 9 Hog pancreas lipase, 29 Porcine pancreas lipase, 26 and Yarrowia lipolytica lipases. 30 However, enzyme catalyzed resolution process is associated with several disadvantages such as higher cost, low substrate concentration, instability and cofactor dependency of the enzymes in several occasions.…”

Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol

“…3,5 Enantiomerically pure 3-alkyl-3-phenyl propanols are used as intermediates in the asymmetric synthesis of antibacterial agents such as curcuphenol, curcuphenone and curcuhydroquinone, 6 in the synthesis of bisabolene sesquiterpenes such as turmerone, a natural cytotoxic agent from Curcuma longa 1 and in the synthesis of the synthetic fragrant florhydral. 7 3-Alkyl-3-phenyl propanols can be oxidized into the corresponding acids or aldehydes, which are used in the synthesis of some diazoketone derivatives, which in turn have been used in Buchner cyclization reactions.…”