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
Hauptverfasser:	Antonchick, Andrey P., Schuster, Hannah, Bruss, Hanna, Schürmann, Markus, Preut, Hans, Rauh, Daniel, Waldmann, Herbert
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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