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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Bibliographic Details
Published in:Tetrahedron 2011-12, Vol.67 (52), p.10195-10202
Main Authors: Antonchick, Andrey P., Schuster, Hannah, Bruss, Hanna, Schürmann, Markus, Preut, Hans, Rauh, Daniel, Waldmann, Herbert
Format: Article
Language:English
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
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.04.056