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Starting from methyl 1, 4-dimethoxynaphthalene-2- acetate (4), (−)-5-deoxy juglomycin A (3) has been prepared in 6 steps; the overall yield is 79%. The key step in the synthesis is the asymmetric hydroxylation of the β, γ-unsaturated ester (8), leading to the hydroxylactone (9) having 96% ee.
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Mohan et al. (1993) studied this question.
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