Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-ones: A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity.
نویسندگان
چکیده
Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one and its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.
منابع مشابه
Synthesis of aminoalkanol derivatives of 4-hydroxy-1,7,8,9,10-pentamethyl-4-aza-tricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione as potential beta-adrenolytics.
A series of aminoalkanol derivatives of 4-hydroxy-1,7,8,9,10-pentamethyl-4-aza-tricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione have been prepared. The pharmacological profile of selected compounds was evaluated for their affinities at beta-adrenoreceptors.
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gepirone, ipsapirone, tandospirone and others) are 1arylpiperazine derivatives with a high affinity to the 5HT1A receptor (1-3). Therefore, they are widely used in the treatment of psychotic and neurotic disorders. This paper is a continuation of our research in the field of 4aryl/heteroaryl piperazinylalkyl derivatives (4, 5) of 1(1H-pyrrole-1-ylmethyl)-10-oxa-azatricyclo[5.2.1.0] dec-8-ene-3,...
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متن کاملSYNTHESIS OF NORBORNENE FURYL ESTERS AND THEIR ENZYMATIC KINETIC RESOLUTION BY PIG LIVER ESTRASE (PLE)
The reaction of furylacrylic acid with cyclopentadiene in toluene gave the expected Diels-Alder endo-and exo-adductsin -1 : 1 ratio. The adducts were separated by iodolactonization method to provide 3-endo-(2'-furyl) bicyclo 12.2.11 hept-5-ene- 2-exo-carboxylic acid and 3-exo-(2'-fury1)bicyclo 12.2.11 hept-5-ene-2-endocarboxylic acid. Esterification of these acids by MeI / HMPA gave the exp...
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عنوان ژورنال:
- The Journal of organic chemistry
دوره 61 20 شماره
صفحات -
تاریخ انتشار 1996