96850-02-1Relevant academic research and scientific papers
Process for preparing seed germinating stimulants
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, (2008/06/13)
Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.
A New Synthetic Route to (+/-)-Strigol
Dailey, Oliver D.
, p. 1984 - 1989 (2007/10/02)
A new more facile synthetic route to strigol, a potent weed seed germination stimulant, utilizes as starting material ethyl 4-oxo-2,6,6-trimethylcyclohex-2-ene-1-carboxylate (2), obtained by the condensation of mesityl oxide and ethyl acetoacetate.Compound 2 was converted in six steps in 38percent overall yield to the previously reported strigol intermediate, 1,4-dioxo-7,7-dimethyl-4,5,6,7-tetrahydro-2-indanacetic acid (11).The new approach is based upon inexpensive starting materials and reagents and is suitable for large-scale production.The key features of the synthesis include reduction of enone 2 to olefin 5 with triethylsilane and boron trifluoride etherate and a one-pot conversion of ethyl 2-(bromomethyl)-6,6-dimethyl-3-oxocyclohex-1-ene-1-carboxylate (10) to the diketo acid 11.
