Asymmetric synthesis of (+)-altholactone, a styryllactone from various goniothalamus species
A consice and stereoselective route to highly functionalised a,b-unsaturated-d-lactone, (+)-altholactone (1), from the well-established 1,3-diol building block, dioxanone (2,2-dimethyl-1,3-dioxan-5-one) 4, is described. This approach is based on establishment of the chiral centres by applying a RAMP-directed alkylation (ee > 98 %), an asymmetric aldol reaction (ee, de > 98 %) and a selective reduction (de > 96 %). The d-lactone, which is the main motif of the styryllactone family, results from an oxidation/in situ cyclisation sequence and the furanic cycle from an SN2 ring-closure.
info:eu-repo/classification/ddc/540, Chemie, asymmetric synthesis, Styryllactone, asymmetric alkylation, aldol reaction
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