Tetrahedron

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

TK Chakraborty, S Purkait, S Das

文献索引：Chakraborty, Tushar K.; Purkait, Subhas; Das, Sanjib Tetrahedron, 2003 , vol. 59, # 46 p. 9127 - 9135

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被引用次数: 18

摘要

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.