Total synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl aza-Claisen rearrangement

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2825-2827

  Roe, Jennifer M ^a   Webster, Richard A B ^b   Ganesan, A ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; HEXAHYDRO[2,3 B]PYRROLOINDOLE; INDOLE ALKALOID; INDOLE DERIVATIVE; OKARAMINE J; PRENYLAMINE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CLAISEN REARRANGEMENT; DRUG SYNTHESIS; PRENYLATION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0141631742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034822n     Document Type: Article

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31. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
32. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
33. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
34. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
35. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
36. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
37. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
38. For charge-accelerated aza-Claisen rearrangements, see: (a) Takamatsu, N.; Inoue, S.; Kishi, Y. Tetrahedron Lett. 1971, 4661-4664. (b) Schmid, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 105-124. (c) Jolidon, S.; Hansen, H.-J. Helv. Chim. Acta 1977, 60, 978-1032. (d) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515-1573. (e) Lai, G.; Anderson, W. K. Tetrahedron Lett. 1993, 34, 6849-6852. (f) Beholz, L. G.; Stille, J. R. J. Org. Chem. 1993, 58, 5095-5100. (g) Anderson, W. K.; Lai, G. Synthesis 1995, 1287-1289. (h) Lai, G.; Anderson, W. K. Tetrahedron 2000, 56, 2583-2590. (i) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621-625.
39. Portions of this work were disclosed at: (a) Royal Society of Chemistry, Perkin Division Southwest Regional Meeting, Swansea, United Kingdom, 16th December, 2002. (b) Cambridge Healthtec Institute, Advancing Library Design and Organic Synthesis, San Diego, 24th February, 2003.
40. Portions of this work were disclosed at: (a) Royal Society of Chemistry, Perkin Division Southwest Regional Meeting, Swansea, United Kingdom, 16th December, 2002. (b) Cambridge Healthtec Institute, Advancing Library Design and Organic Synthesis, San Diego, 24th February, 2003.