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Total synthesis and structure confirmation of elatenyne: success of computational methods for NMR prediction with highly flexible diastereomers.
TLDR
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.
TLDR
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.
TLDR
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.
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