Objective
The conjugate addition of nucleophiles followed by annulation will be explored for R-(-)- and/or S-(+)-carvone, in order to obtain highly functionalised chiral decalones. Wageningen has a broad experience with S-(+)-carvone as chiral starting material in the syntheses of insect antifeedants, flavour compounds and other sesquiterpenes and in Valencia the total synthesis of sesquiterpenes is one of the main research subjects. The steroid laboratory in Minsk has a long-standing reputation for its work in the field of steroid synthesis.
A new and promising development in the chemistry of carvone starts with a conjugate addition of potassium cyanide to the enone in carvone, followed by an annulation reaction. In this way chiral 3-decalones with a C9-nitril group and a potential functional group at C7 can be obtained in an easy sequence and in high yield. The application of these chiral decalones in the synthesis of steroids and of other useful sesquiterpenes will be investigated in all three laboratories.
Structural fragments that have to be used as starting material for the AB steroid rings will be synthesized from these 9-cyano-3-decalones. The construction of the C,D steroid ring fragments will be investigated starting from S-(+)-carvone or from other suitable starting materials. The AB- and CD-steroid ring fragments will finally be combined to complete the steroid skeletons. The steroid group in Minsk has broad experience in this field and most of this research will be performed there.
Ring transformation of the six membered ring compounds into five membered ring D fragments, accompanied by investigations of new methods for the removal of the isopropenyl group, will be investigated in Wageningen. The conjugate addition of other suitable nucleophiles to S-(+)-carvone and the conversion of the adducts obtained into steroids and sesquiterpenes will be investigated in Wageningen and in Valencia.
The investigation of abundantly available natural products for use as chiral starting material in the synthesis of useful products in the field of flavours and fragrances, therapeutics, and crop protecting agents, is a general theme in all the research that will be performed in the context of this programme.
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Programme(s)
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Coordinator
6703 HB Wageningen
Netherlands
The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.