Nonstabilized N-unsubstituted azomethine ylides: A synthesis of indolizidine 239CD

Organic Letters

Volumn 1, Issue 2, 1999, Pages 349-351

  Clark, Roger B ^a   Pearson, William H ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE 239CD; INDOLIZINE DERIVATIVE;

ANIMAL; ARTICLE; FROGS AND TOADS; POISONOUS ANIMAL; SYNTHESIS;

ANIMALS; ANIMALS, POISONOUS; ANURA; INDOLIZINES;

EID: 0033614873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990677v     Document Type: Article

References (38)

1. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1999, in press.
2. For a related approach using other electrophiles to initiate the formation of azomethine ylides from (2-azaallyl)stannanes, see: Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441-5444.
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9. Azomethine ylides have been used to make indolizidines and pyrrolizidines. See: refs 2 and 3c-e above and (a) Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27, 981-1008.
10. (b) Pandey, G.; Lakshmaiah, G.; Ghatak, A. Tetrahedron Lett. 1993, 34, 7301-4. During the course of this work, a related approach to indolizidines and pyrrolizidines involving the dipolar cycloaddition of stabilized azomethine ylides with alkenes followed by intramolecular reductive amination was published. See:
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19. Many syntheses of these and related indolizidines have been published. For the latest in a series of reviews covering the synthesis of indolizidines and pyrrolizidines, see: (a) Michael, J. P. Nat. Prod. Rep. 1998, 15, 571-594. For syntheses of indolizidines 195B, 223AB, 239AB, and 239CD by an approach involving trans-2,5-disubstituted pyrrolidines, see:
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36. See ref 17 for a comparison with existing methods for the generation of nonstabilized N-substituted and N-unsubstituted azomethine ylides. Regarding nonstabilized N-unsubstituted azomethine ylides, two other methods for their generation are known, the decarboxylation of imines derived from the condensation of α-amino acids with aldehydes [leading references: (a) Tsuge, O.; Kanemasa, S.; Ohe, M.; Takenaka, S. Bull. Soc. Chem. Jpn. 1987, 60, 4079-4089.
37. (b) Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1988, 44, 4953-4966] and the water-induced generation of such ylides from N-(silylmethyl)imines [Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Bull. Soc. Chem. Jpn. 1986, 59, 2537-2545]. The first method suffers from low yields and poor trans:cis stereoselectivity, while the second is limited to nonenolizable imines with no branching next to silicon (i.e., monosubstituted azomethine ylides).
38. (b) Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1988, 44, 4953-4966] and the water-induced generation of such ylides from N-(silylmethyl)imines [Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Bull. Soc. Chem. Jpn. 1986, 59, 2537-2545]. The first method suffers from low yields and poor trans:cis stereoselectivity, while the second is limited to nonenolizable imines with no branching next to silicon (i.e., monosubstituted azomethine ylides).