Enantioselective synthesis of the spirotryprostatin A scaffold
The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex...
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| Veröffentlicht in: | Tetrahedron 2011-12, Vol.67 (52), p.10195-10202 |
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| container_end_page | 10202 |
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| container_issue | 52 |
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| container_title | Tetrahedron |
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| creator | Antonchick, Andrey P. Schuster, Hannah Bruss, Hanna Schürmann, Markus Preut, Hans Rauh, Daniel Waldmann, Herbert |
| description | The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex 3,3′-pyrrolidinyl-spirooxindole core with Fmoc-proline and spontaneous ring closure upon N-deprotection.
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| doi_str_mv | 10.1016/j.tet.2011.04.056 |
| format | Article |
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| ispartof | Tetrahedron, 2011-12, Vol.67 (52), p.10195-10202 |
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| language | eng |
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| subjects | 1,3-Dipolar cycloaddition [3+2] Cycloaddition All-carbon quaternary spirocenter Biology-oriented synthesis Chemistry Closures Cycloaddition Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties Scaffolds Spirotryprostatin A Spontaneous Synthesis (chemistry) Tetrahedrons |
| title | Enantioselective synthesis of the spirotryprostatin A scaffold |
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