The total synthesis of (-)-amathaspiramide F

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4556-4559

  Hughes, Chambers C ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Alkaloids; Amathaspiramides; Nef reaction; Proline; Total synthesis

Indexed keywords

CHEMICAL ANALYSIS; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

CHIRALITY;

STEREOCHEMISTRY;

ACETAL DERIVATIVE; ALKALOID; AMATHASPIRAMIDE F; NATURAL PRODUCT; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; BRYOZOA; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MARINE ENVIRONMENT; NEW ZEALAND; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ACETALS; ALKALOIDS; ANIMALS; BRYOZOA; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; PYRROLIDINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0037011216     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4556::AID-ANIE4556>3.0.CO;2-E     Document Type: Article

References (28)

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15. -3. CCDC-188930 (13a) and CCDC-192396 (17) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
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17. 3, an unexpected cyclization occurred that (to our knowledge) represents a conceptually novel method for synthesizing hydrazones:
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19. For recent applications of the TFA protecting group, see: a) K. C. Nicolaou, B. S. Safina, C. Funke, M. Zak, F. J. Zécri, Angew. Chem. 2002, 114, 2017-2020; Angew. Chem. Int. Ed. 2002, 41, 1937-1940; b) M. W. Carson, G. Kim. M. F. Hentemam, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4582-4584; Angew. Chem. Int. Ed. 2001, 40, 4450-4452; c) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456.
20. For recent applications of the TFA protecting group, see: a) K. C. Nicolaou, B. S. Safina, C. Funke, M. Zak, F. J. Zécri, Angew. Chem. 2002, 114, 2017-2020; Angew. Chem. Int. Ed. 2002, 41, 1937-1940; b) M. W. Carson, G. Kim. M. F. Hentemam, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4582-4584; Angew. Chem. Int. Ed. 2001, 40, 4450-4452; c) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456.
21. For recent applications of the TFA protecting group, see: a) K. C. Nicolaou, B. S. Safina, C. Funke, M. Zak, F. J. Zécri, Angew. Chem. 2002, 114, 2017-2020; Angew. Chem. Int. Ed. 2002, 41, 1937-1940; b) M. W. Carson, G. Kim. M. F. Hentemam, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4582-4584; Angew. Chem. Int. Ed. 2001, 40, 4450-4452; c) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456.
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23. For recent applications of the TFA protecting group, see: a) K. C. Nicolaou, B. S. Safina, C. Funke, M. Zak, F. J. Zécri, Angew. Chem. 2002, 114, 2017-2020; Angew. Chem. Int. Ed. 2002, 41, 1937-1940; b) M. W. Carson, G. Kim. M. F. Hentemam, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4582-4584; Angew. Chem. Int. Ed. 2001, 40, 4450-4452; c) M. W. Carson, G. Kim, S. J. Danishefsky, Angew. Chem. 2001, 113, 4585-4588; Angew. Chem. Int. Ed. 2001, 40, 4453-4456.
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26. All attempts to perform a one-pot Nef reaction on 19 to afford 21 directly were unsuccessful.
27. Deprotection with sodium tetrahydroborate in ethanol resulted in significant reduction of the hemiaminal function,
28. The large discrepancy in value of the optical rotation is perhaps due to the low concentration of the natural sample.