1.
J Org Chem
; 61(20): 6931-6935, 1996 Oct 04.
Artigo
em Inglês
| MEDLINE
| ID: mdl-11667588
RESUMO
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.