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- W2951856544 abstract "Methods for highly stereocontrolled syntheses of chiral building blocks with a triad of contiguous stereocenters, including two quaternary ones, have been developed. Ireland–Claisen rearrangement of the (Z)-silyl ketene acetal generated stereoselectively from the (R)-3-methylcyclohex-2-enyl ester derived from an acyclic carboxylic acid proceeded through a chairlike transition state to give the rearranged product with an S configuration at the position α to the carboxyl group. Introduction of a cyclic conformational constraint in the acid component completely switched the transition state of the rearrangement to a boatlike one, leading to the predominant formation of a product with an R configuration, from which pseudodiastereomeric α-hydroxy esters were obtained in a four-step sequence. The enyne obtained through a base-mediated double eliminative ring-opening reaction was successfully converted into advanced intermediates for the synthesis of 9-oxygenated labdane diterpenoids through a Heck reaction and a regioselective transformation of the resultant diene." @default.
- W2951856544 created "2019-06-27" @default.
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- W2951856544 date "2013-12-23" @default.
- W2951856544 modified "2023-09-29" @default.
- W2951856544 title "Synthesis of Chiral Building Blocks for Oxygenated Terpenoids through a Simultaneous and Stereocontrolled Construction of Contiguous Quaternary Stereocenters by an Ireland–Claisen Rearrangement" @default.
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- W2951856544 doi "https://doi.org/10.1021/jo402537u" @default.
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