Total synthesis of ()-xyloketal D and its enantiomer Confirmation of absolute stereochemistry

JD Pettigrew, RP Freeman…

Index: Pettigrew, Jeremy D.; Freeman, Rebecca P.; Wilson, Peter D. Canadian Journal of Chemistry, 2004 , vol. 82, # 11 p. 1640 - 1648

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Citation Number: 37

Abstract

The total synthesis of ()-xyloketal D and its enantiomer have been achieved by the reaction of an ortho-quinone methide with (4 R)-and (4 S)-4, 5-dihydro-2, 4-dimethylfuran via a diastereoselective inverse electron demand Diels Alder reaction. This total synthesis confirmed the absolute stereochemistry of the natural product. The ortho-quinone methide was generated by reaction of an appropriately functionalized Mannich base with methyl ...