Chiral η6-arene-Cr(CO)3 complexes in organic synthesis: A short and highly selective synthesis of the 18-nor-seco-pseudopterosin aglycone

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4545-4548

  Majdalani, André ^a   Schmalz, Hans Günther ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; TETRALIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; STEREOISOMERISM;

ARENE;

EID: 0030913414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00995-7     Document Type: Article

References (37)

1. 3 chemistry in synthesis, see, for instance: a) Hegedus, L.S. Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994, chapter 10;
2. b) Semmelhack, M.F. in Comprehensive Organometallic Chemistry II, Vol. 12, Abel, E.W.; Stone, F.G.A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, pp. 979-1015;
3. c) Semmelhack, M.F., ibid., pp. 1017-1038;
4. d) Davies, S.G.; McCarthy, T.D.; ibid. pp. 1039-1070.
5. For some recent publications in this series, see: a) Schmalz, H.-G.; Schwarz, A.; Dürner, G. Tetrahedron Lett. 1994, 35, 6861;
6. b) Schmalz, H.-G.; Majdalani, A.; Geller, T., Hollander, J. Bats, J. W. Tetrahedron Lett. 1995, 36, 4777;
7. c) Schmalz, H.-G.; Siegel, S.; Schwarz, A. Tetrahedron Lett. 1996, 37, 2947;
8. d) Schmalz, H.-G.; Schellhaas, K. Angew. Chem. 1996, 108, 2277; Angew. Chem. Int. Ed. Engl. 1996, 35, 2146;
9. d) Schmalz, H.-G.; Schellhaas, K. Angew. Chem. 1996, 108, 2277; Angew. Chem. Int. Ed. Engl. 1996, 35, 2146;
10. e) see ref. 3.
11. a) Schmalz, H.-G.; Hollander, J.; Arnold, M.; Dürner, G. Tetrahedron Lett. 1993, 34, 6259;
12. b) Schmalz, H.-G.; Arnold, M.; Hollander, J.; Bats, J.W. Angew. Chem. 1994, 106, 77; Angew. Chem. Int. Ed. Engl. 1994, 33, 109.
13. b) Schmalz, H.-G.; Arnold, M.; Hollander, J.; Bats, J.W. Angew. Chem. 1994, 106, 77; Angew. Chem. Int. Ed. Engl. 1994, 33, 109.
14. a) Look, S.A.; Fenical, W. Tetrahedron 1987, 43, 3363;
15. b) for a total synthesis of the racemic seco-pseudopterosin aglycone, see: McCombie, S.W.; Cox, B.; Lin, S.-I.; Ganguly, A.K.; McPhail, A.T. Tetrahedron Lett. 1991, 32, 2083;
16. c) for a recent synthetic approach to the pseudopterosins via seco-intermediates, see: Gill, S.; Kociensky, P.; Kohler, A.; Pontiroli, A,; Qun, L. J. Chem. Soc., Chem. Commun. 1996, 1743.
17. a) Tippet, L.M.; Massy-Westtropp, R.A. Phytochem. 1993, 35, 417;
18. b) Croft, K.D.; Ghisalberti, E.L.; Jefferies, P.R.; Proudfoot, G.M. Aust. J. Chem. 34, 1951.
19. We have recently completed a synthesis of the seco-pseudopterosin aglycone using a different strategy, see: a) Majdalani, A.; Schmalz, H.-G. manuscript in preparation;
20. b) for a synthesis of dihydroxyserrulatic acid employing racemic chromium arene complexes, see: Uemura, M.; Nishimura, M., Minami, T., Hayashi, Y. J. Am. Chem. Soc. 1991, 113, 5402.
21. 3 derivatives, see: a) Semmelhack, M.F.; Seufert, W.; Keller, L. J. Am. Chem. Soc. 1980, 102, 6584;
22. b) Uemura, M.; Minami, T.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1984, 1193;
23. c) see also ref. 1b and references cited therein.
24. All Compounds were fully characterized by the usual spectroscopic methods and gave correct elemental analyses and/or HRMS data; yields refer to the pure products after flash chromatography and/or recrystallization.
25. a) Schmalz, H.-G.; Millies, B.; Bats, J.W.; Dürner, G. Angew. Chem. 1992, 104, 640; Angew. Chem., Int. Ed. Engl. 1992, 31, 631;
26. a) Schmalz, H.-G.; Millies, B.; Bats, J.W.; Dürner, G. Angew. Chem. 1992, 104, 640; Angew. Chem., Int. Ed. Engl. 1992, 31, 631;
27. b) see ref. 2b.
28. 3 in THF following the general procedure of Imamoto; for a review, see: Imamoto, T. Pure Appl. Chem. 1990, 62, 747.
29. a) Peterson, D.J. J. Org. Chem. 1968, 33, 780;
30. b) Ager, D.J. Org. Reactions 1990, 38, 1.
31. 3): δ = 21.9 (t), 24.3 (t), 31.7 (t), 56.1 (q), 65.3 (q), 73.3 (d), 87.0 (d), 95.9 (s), 109.5 (s), 109.6 (t), 127.6 (s), 135.8 (s), 139.6 (s), 233.8 (s).
32. 3): δ = -0.1 (q), 20.2 (q), 26.2 (t), 28.0 (t), 28.1 (t), 60.6 (q), 65.2 (q), 90.3 (s), 93.3 (d), 95.8 (s), 110.0 (t), 115.2 (s), 131.3 (s), 138.9 (s), 139.6 (s), 233.6 (s).
33. 2O at -25 °C.
34. 3): δ = 17.7 (q), 19.8 (t), 20.3 (q), 24.4 (t), 25.7 (q), 27.7 (t), 28.2 (d), 33.5 (d), 38.6 (t), 55.6 (q), 66.3 (q), 71.3 (d), 94.2 (d), 106.4 (s), 118.6 (s), 124.1 (d), 126.0 (s), 131.8 (s), 137.2 (s), 234.5 (s);
35. 3): δ = 15.5 (q), 17.7 (q), 20.3 (q), 20.5 (t), 24.9 (t), 25.7 (q), 27.8 (t), 27.9 (d), 28.3 (t), 33.8 (d), 37.7 (t), 60.8 (q), 65.1 (q), 95.2 (d), 98.1 (s), 109.2 (s), 115.6 (s), 124.2 (d), 131.5 (s), 131.7 (s), 134.5 (s), 234.4 (s).
36. 3): δ = 15.7 (q), 17.7 (q), 20.4 (t), 22.0 (q), 24.9 (t), 25.7 (q), 27.2 (d), 28.1 (t), 28.3 (t), 37.1 (d), 37.4 (t), 59.7 (q), 60.2 (q), 124.7 (d), 126.1 (d), 129.1 (s), 131.3 (s), 133.5 (s), 137.4 (s), 148.8 (s), 150.4 (s), 234.4 (s).
37. 3 was run at higher temperatures (20 °C) a side-product resulting from hydrochlorination of the sidechain doublebond was formed in high yield.