Total synthesis of anachelin H

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4707-4710

  Gademann, Karl ^a   Bethuel, Yann ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANACHELIN H; NATURAL PRODUCT; POLYKETIDE; SERINE; TELLURIUM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; QUINOLINIUM COMPOUNDS; SERINE; STEREOISOMERISM;

EID: 11444262619     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048068x     Document Type: Article

References (27)

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2. Beiderbeck, H.; Taraz, K.; Budzikiewicz, H.; Walsby, A. E. Z. Naturforsch. 2000, 55c, 681-687. Beiderbeck, H. Ph.D. Dissertation, Universität zu Köln, Köln, 2000. Anachelin was probably isolated 30 years ago, but its constitution could not be elucidated; see: Walsby, A. E. Br. Phycol. J. 1974, 9, 383-391.
3. Beiderbeck, H.; Taraz, K.; Budzikiewicz, H.; Walsby, A. E. Z. Naturforsch. 2000, 55c, 681-687. Beiderbeck, H. Ph.D. Dissertation, Universität zu Köln, Köln, 2000. Anachelin was probably isolated 30 years ago, but its constitution could not be elucidated; see: Walsby, A. E. Br. Phycol. J. 1974, 9, 383-391.
4. Itou, Y.; Okada, S.; Murakami, M. Tetrahedron 2001, 57, 9093-9099.
5. Reviews: Keller-Schierlein, W.; Prelog, V.; Zahner, H. Fort. Chem. Org. Nat. 1964, 22, 279-322. Raymond, K. N.; Muller, G.; Matzanke, B. F. Top. Curr. Chem. 1984, 123, 49-102. Drechsel, H.; Jung, G. J. Pept. Sci. 1998, 4, 147-181.
6. Reviews: Keller-Schierlein, W.; Prelog, V.; Zahner, H. Fort. Chem. Org. Nat. 1964, 22, 279-322. Raymond, K. N.; Muller, G.; Matzanke, B. F. Top. Curr. Chem. 1984, 123, 49-102. Drechsel, H.; Jung, G. J. Pept. Sci. 1998, 4, 147-181.
7. Reviews: Keller-Schierlein, W.; Prelog, V.; Zahner, H. Fort. Chem. Org. Nat. 1964, 22, 279-322. Raymond, K. N.; Muller, G.; Matzanke, B. F. Top. Curr. Chem. 1984, 123, 49-102. Drechsel, H.; Jung, G. J. Pept. Sci. 1998, 4, 147-181.
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13. 1H NMR.
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15. Narasaka, K.,; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238.
16. Chen, K.-M.; Hardtmann, G. E.; Prasad, G. E.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. See also: Sletzinger, M.; Verhoeven, T. R.; Volante, R. P.; McNamara, J. M.; Corley, E. G.; Liu, T. M.H. Tetrahedron Lett. 1985, 26, 2951-2954.
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19. Diastereoselectivities were greater than 96:4 for 7 and greater than 97:3 for 9.
20. See Supporting Information for procedures nd analytical data of all new compounds.
21. See Supporting Information for the corresponding spectra.
22. This compound is readily available from L-DOPA in two steps; see ref 4.
23. Ley, S. V.; Meerholz, C. A.; Barton, D. H. R. Tetrahedron 1981, 37, 213-223. For a related application, see: Clews, J.; Cooksey, C. J.; Garratt, P. J.; Land, E. J.; Ramsden, C. A.; Riley, P. A. J. Chem. Soc., Perkin Trans, 1 2000, 4306-4315.
24. Ley, S. V.; Meerholz, C. A.; Barton, D. H. R. Tetrahedron 1981, 37, 213-223. For a related application, see: Clews, J.; Cooksey, C. J.; Garratt, P. J.; Land, E. J.; Ramsden, C. A.; Riley, P. A. J. Chem. Soc., Perkin Trans, 1 2000, 4306-4315.
25. f values on TLC.
26. We thank Prof. Dr. H. Budzikiewicz for an authentic sample of Anachelin H.
27. A change in pH could also induce other structural changes such as different protonation state or a change in conformation. For the solution structure of anachelin H, see: Gademann, K.; Budzikiewicz, H. Chimia 2004, 58, 212-214.