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- W86448634 abstract "Phyllaemblic acid is a highly oxygenated natural product isolated along with a number of related compounds from the roots of Phyllanthis emblica L. by Zhang et al. in 2000.The roots of this shrub have been used by the people in south-east Asia as an antiscorbutic and in the treatment of diverse ailments, especially those associated with the digestive organs. A total synthesis has yet to be reported.A concise sequence has been developed which rapidly furnishes a range of meso bridged bicyclic ketones, in good yield and with complete diastereocontrol, utilizing on an α,α’-annelation reaction of 1,3-dioxan-5-ones. The bicyclic systems are shown to adopt chair-boat conformations in both solution and in the solid state. Singlediastereomers are obtained in two cases with two different substituents. Stereochemical outcomes have been rationalized using steric and stereoelectronic arguments.Carbon-carbon bond formation at the ketone carbonyl in these bicyclic systems is shown to be problematic. Ortho-acetal hydrolysis and diol reprotection as a bis-TBS ether provides a monocyclic system with increased ketone reactivity, allowing elaboration to an α-hydroxyaldehyde of appropriate stereochemistry for future application in a synthesis of the natural product. Preliminary studies towards this goal on a simplified model system are reported." @default.
- W86448634 created "2016-06-24" @default.
- W86448634 creator A5068841436 @default.
- W86448634 date "2013-07-01" @default.
- W86448634 modified "2023-09-23" @default.
- W86448634 title "Studies toward the total synthesis of phyllaemblic acid" @default.
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- W86448634 hasPublicationYear "2013" @default.
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