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- W2073931561 abstract "We report the joint application of ab initio computations and total synthesis to assign the absolute configuration of a new natural product. The expected specific rotations of the (7S,10R)- and (7R,10R)-isomers of pitiamide A in a CHCl3 solvent continuum model were determined as +8 and −39, respectively, by CADPAC calculations of the electric-dipole−magnetic-dipole polarizability tensor. Total syntheses of these two stereoisomers of the marine metabolite were achieved by a convergent strategy that utilized Evans' oxazolidinone alkylation, a novel water-accelerated modification of Negishi's zirconocene-catalyzed asymmetric carbometalation as well as an unusual segment condensation via Mitsunobu alkylation of a nosyl-activated amide. The experimental optical rotation measurements confirmed the results of the computational optical rotation predictions. On the basis of NMR comparisons, the configuration of pitiamide A was assigned as (7R,10R). These studies highlight the considerable structural significance o..." @default.
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- W2073931561 date "2010-06-03" @default.
- W2073931561 modified "2023-09-25" @default.
- W2073931561 title "ChemInform Abstract: Optical Rotation Computation, Total Synthesis, and Stereochemistry Assignment of the Marine Natural Product Pitiamide A." @default.
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- W2073931561 doi "https://doi.org/10.1002/chin.200034214" @default.
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