Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.02,6]dec-8-en-3-ones: A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (20) , 6931-6935
- https://doi.org/10.1021/jo9610220
Abstract
Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.02,6]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.Keywords
This publication has 9 references indexed in Scilit:
- Stimulation of Orobanche crenata Seed Germination by (+)-Strigol and Structural Analogues Dependence on Constitution and Configuration of the Germinatio StimulantsJournal of Plant Physiology, 1993
- Isolation of strigol, a germination stimulant for Striga asiatica, from host plantsJournal of Agricultural and Food Chemistry, 1993
- Germination stimulants produced by Vigna unguiculata Walp cv Saunders UprightJournal of Plant Growth Regulation, 1992
- A Germination Stimulant for Parasitic Flowering Plants from Sorghum bicolor, a Genuine Host PlantJournal of Plant Physiology, 1992
- Synthesis and biological evaluation of A‐ring analogs of the natural germination stimulant strigolRecueil des Travaux Chimiques des Pays-Bas, 1992
- Asymmetric Diels-Alder reactions with 5-menthyloxy-2-(5H)-furanoneTetrahedron: Asymmetry, 1991
- Advanced Organic ChemistryPublished by Springer Nature ,1990
- New general asymmetric synthesis of versatile .gamma.-alkylated butenolides and its application to expeditious synthesis of the chiral Geissman-Waiss lactones useful for (+)-retronecine synthesisThe Journal of Organic Chemistry, 1989
- 4-Hydroxy-2-butenolide. A versatile reagent for the synthesis of heterocyclic compoundsThe Journal of Organic Chemistry, 1982