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Total synthesis and structure confirmation of elatenyne: success of computational methods for NMR prediction with highly flexible diastereomers.
The total synthesis of elatenyne demonstrates that DFT calculations of (13)C NMR chemical shifts coupled with biosynthetic postulates, comprise a very useful method for distinguishing among large numbers of highly flexible, closely related molecules.
Stereostructure assignment of flexible five-membered rings by GIAO 13C NMR calculations: prediction of the stereochemistry of elatenyne.
It is shown that calculation of (13)C NMR chemical shifts using the geometries obtained using molecular mechanics greatly reduces the computational expense without a significant loss of accuracy, even in this demanding system.
Structure Reassignment of Laurefurenynes A and B by Computation and Total Synthesis
The originally assigned stereostructures of laurefurenynes A and B have been reassigned on the basis of DFT calculations of NMR chemical shifts, synthesis of model compounds and total synthesis of
Synthesis of (+)-obtusenyne.
An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen
Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula.
A bidirectional synthesis of the originally proposed structures for the natural products elatenyne and a chloroenyne from Laurencia majuscula is described along with a reassessment of the structures
The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles.
The synthesis of five fused-bicyclic medium-ring lactones carrying identical ring-fusion to that in the polyether toxins is described using an enolate hydroxylation, intramolecular hydrosilation,
A Total Synthesis of Salinosporamide A.
A short synthesis of Salinosporamide A is reported, that uses an oxidative radical cyclization as a key step and allows for the preparation of gram quantities of advanced synthetic intermediates.