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Allenamide‐Initiated Cascade [2+2+2] Annulation Enabling the Divergent Total Synthesis of (−)‐Deoxoapodine, (−)‐Kopsifoline D and (±)‐Melotenine A.
- Source :
- Angewandte Chemie International Edition; 8/22/2022, Vol. 61 Issue 34, p1-7, 7p
- Publication Year :
- 2022
-
Abstract
- A facile method for the construction of the aspidosperma core from indoles functionalized with a nonterminal N‐allenamide and dimethyl methylenemalonate is described. Various polysubstituted tetracyclic spiroindolines (27 examples) were afforded in good yields (61–90 %) with >99/1 dr and >99/1 Z/E selectivity under mild conditions. The annulation reaction provides straightforward access to the tetracyclic spiroindoline skeleton with substituents at the C5 position occurring in many natural products. As an application of this reaction, the total synthesis of three important natural products, (−)‐deoxoapodine, (−)‐kopsifoline D and (±)‐melotenine A, was possible in short routes from tryptamine. [ABSTRACT FROM AUTHOR]
- Subjects :
- ANNULATION
NATURAL products
INDOLINE
INDOLE alkaloids
TRYPTAMINE
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 61
- Issue :
- 34
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 158571935
- Full Text :
- https://doi.org/10.1002/anie.202207360