Enantioselective synthesis of a Wieland-Miescher ketone bearing an angular hydroxymethyl group

Synthetic Communications

Volumn 26, Issue 5, 1996, Pages 945-961

  Hanselmann, Roger ^a   Benn, Michael ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; QUINONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030013187     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003699     Document Type: Article

References (32)

1. a) Renard, P. Y.; Lallemand, J. Y. Synlett 1993, 163
2. b) Schwerdtfeger, A. E.; Chan, T. H , Thomas, A. W., Strunz, G. M.; Salonius, A.; Chiasson, M. Can. J. Chem. 1993, 71, 1184
3. c) Lejeune, J.; Lallemand, J. Y. Tetrahedron Lett. 1992, 33, 2977
4. d) Schwerdtfeger, A. E.; Chan, T. H. J. Org. Chem. 1991, 56, 3294
5. e) Liu, H. J.; Ulibarri, G.; Nelson, L. A. K. J. Chem. Soc. Chem. Commun. 1990, 1419
6. f) Hagiwara, H.; Uda, H. J. Chem. Soc. Perkin Trans. 1, 1990, 1901
7. g) Tamai, Y.; Hagiwara, H , Uda, H. J. Chem. Soc. Perkin Trans. 1 , 1986, 1311
8. h) Liu, H. J.; Ngooi, T. K. Can. J. Chem. 1984, 62, 2676
9. i) Ley, S. V.; Neuhaus, D.; Simpkins, N. S.; Whittle, A. J. J. Chem. Soc. Perkin Trans. 1 , 1982, 2157
10. j) Jackson, W. P.; Ley, S. V. J. Chem. Soc. Perkin Trans. 1, 1981, 1516
11. k) Luteijn, J. M.; De Groot, A. J. Org. Chem. 1981, 46, 3448.
12. For remote introduction of a hydroxymethyl group see: a) Burke, S. D ; Silks, L. A.; III; Strickland, S. M. Tetrahedron Lett. 1988, 29, 2761
13. b) Mori, K.; Aki, S. Liebigs Ann. Chem. 1993, 97.
14. Lavalee, J. F.; Spino, C.; Ruel, R.; Hogan, K. T.; Deslongchamps, P. Can. J. Chem. 1992, 70, 1406 and cited herein.
15. Tamai, T.; Mizutani, Y.; Hagiwara, H.; Uda, H.; Harada, N. J. Chem. Research 1 985, (S) 148; (M) 1746.
16. Hamilton, R. J.; Mander, L. N., Sethi, S. P. Tetrahedron 1986, 42, 2881 and cited herein.
17. We tried to cyclizise 1 with several Nazarov reagents (1-phenylsulfinyl-3-buten-2-one, 1-phenylthio-3-buten-2-one, 1-phenylsulfinyl-4-(triethylsilyl)-3-buten-2-one, 1-phenylsulfoxyl-4-(triethylsilyl)-3-buten-2-one, 1-phenylsulfinyl-4-(trimethylsilyl)-3-buten-2-one, methyl-5-(trimethylsilyl)-3-oxo-4-pentenoate), however with no success.
18. a) Buchschacher, P.; Fuerst, A.; Gutzwiller, J. Organic Synthesis. Freeman, J. P., Ed., Wiley: New York, 1990; Coll. Vol. 7; p. 368.
19. b) Agami, C.; Bull. Soc. Chim. Fr. 1988, 3, 499
20. a) Rausch, W.; Venkataramani, P. S. Tetrahedron Lett. 1968, 51, 5283
21. b) Rausch, W.; Grimm, K.; Karoglan, J. E.; Martin, J.; Subrahamanian, K. P.; Toong, Y. C.; Venkataramani, P. s.; Yordi, J. D.; Zoutendam, P., J. Am. Chem. Soc. 1977, 99, 1953.
22. . a) Stetter, H.; Diericks, W. Chem. Ber. 1952, 85, 1061
23. b) Verhé, R.; De Buyck, L.; Schamp, N. Bull. Soc. Chim. Belg. 1975, 84, 761
24. c) Rajamannar, T.; Palani, N.; Balasubramanian, K. K. Synthetic Commun. 1993, 23, 3095.
25. 8 only published a vague description of the amount of NaOH they used (one pellet of NaOH), which was approximated to be roughly 0.05 equivalents.
26. 1H-NMR.
27. Cramer, R J. Am. Chem. Soc. 1966, 88, 2272.
28. Rao, C S. S.; Rajagopalan, K.; Swaminathan, S. Ind. J. Chem. 1982, 21B, 753
29. 4. Ward, D. E.; Rhee, C. K. Can. J. Chem. 1989, 67, 1206
30. During the preparation of this manuscript, Ziegler et al. published a paper in which they used racemic 8 for the total synthesis of (±)-Scopadulcic acid A and B and (±)-Scopadulciol as well as reporting preliminary studies about the synthesis of chiral 8 (Ziegler, E F., Wallace, O. B. J. Org. Chem. 1995, 60, 3626).
31. 8 d 5.8 (m, 1H), 5.2 (m, 3H), 2.0-2.9 (m, 12H). Those data are somewhat erroneous in that H′-3 at 1.70-1.66 ppm was not reported and instead was assumed to be underneath the unresolved multiples between 2.0-2.9 ppm. However, COSY and HSC spectra clearly revealed that this multiplet at 1.70-1.66 ppm has to be assigned to H′-3.
32. Wieland-Miescher ketone numbering