Publication | Closed Access
Studies Directed toward the Total Synthesis of Azaspiracid: Stereoselective Construction of C<sub>1</sub>−C<sub>12</sub>, C<sub>13</sub>−C<sub>19</sub>, and C<sub>21</sub>−C<sub>25</sub> Fragments
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Citations
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References
2000
Year
EngineeringOrganic ChemistryChemistryHeterocycle ChemistryEvans Asymmetric AlkylationStereoselective SynthesisEfficient EntryNeighboring Chiral OxazolidinoneBiochemistryDiversity-oriented SynthesisTotal SynthesisStudies DirectedPharmacologyNatural Product SynthesisAsymmetric CatalysisEnantioselective SynthesisStereoselective ConstructionBiomolecular EngineeringNatural SciencesSynthetic Chemistry
[reaction: see text] The efficient entry to the C(1)-C(12), C(13)-C(19), and C(21)-C(25) fragments of azaspiracid is outlined. The C(1)-C(12) portion is constructed using a key asymmetric allenyl borane addition to the corresponding alpha,beta-unsaturated aldehyde. The synthesis of the C(13)-C(19) portion utilizes an Evans asymmetric alkylation followed by Sharpless asymmetric dihydroxylation. In addition, a novel solution to the mismatched effects of a neighboring chiral oxazolidinone during a Sharpless dihydroxylation is detailed.
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