Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A |
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Authors: | Tushar K Chakraborty Subhas PurkaitSanjib Das |
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Institution: | Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported. |
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Keywords: | epoxy alcohols Sharpless epoxidation epoxide opening macrosphelides |
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