A synthesis of the ring system of terpestacin

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 843-846

  Mermet Mouttet, Marie Paule ^a   Gabriel, Kiroubagaranne ^a   Heissler, Denis ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Macrocycles; McMurry reactions; Terpenes; Wittig reactions

Indexed keywords

SESTERTERPENE; TERPENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0033613786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02535-0     Document Type: Article

References (27)

1. Iimura, S.; Oka, M.; Narita, Y.; Konishi, M.; Kakisawa, H.; Gao, Q.; Oki, T. Tetrahedron Lett. 1993, 34, 493-496. Oka, M.; Iimura, S.; Narita, Y.; Furumai, T.; Konishi, M.; Oki, T.; Gao, Q.; Kakisawa, H. J. Org. Chem. 1993, 58, 1875-1881.
2. Iimura, S.; Oka, M.; Narita, Y.; Konishi, M.; Kakisawa, H.; Gao, Q.; Oki, T. Tetrahedron Lett. 1993, 34, 493-496. Oka, M.; Iimura, S.; Narita, Y.; Furumai, T.; Konishi, M.; Oki, T.; Gao, Q.; Kakisawa, H. J. Org. Chem. 1993, 58, 1875-1881.
3. Takeda, K.; Nakajima, A.; Yoshii, E. Synlett 1995, 249-250.
4. Tatsuta, K.; Masuda, N.; Nishida, H. Tetrahedron Lett. 1998, 39, 83-86.
5. Presented in part at the GECO XXXVIII Meeting, Mittelwihr (France), 24-29 August 1997.
6. Examples of McMurry macrocyclisations are reviewed in: McMurry, J. E. Chem. Rev. 1989, 89, 1513- 1524; Fürstner, A.; Bogdanovic, B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469; Lectka, T. The McMurry reaction. In: Fürstner, A., editor. Active Metals. Weinheim, VCH, 1996, 85-131. A macrocycle bearing an allylic silyl ether is obtained in: Li, Y.; Li, W.; Li, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2953-2956.
7. Examples of McMurry macrocyclisations are reviewed in: McMurry, J. E. Chem. Rev. 1989, 89, 1513- 1524; Fürstner, A.; Bogdanovic, B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469; Lectka, T. The McMurry reaction. In: Fürstner, A., editor. Active Metals. Weinheim, VCH, 1996, 85-131. A macrocycle bearing an allylic silyl ether is obtained in: Li, Y.; Li, W.; Li, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2953-2956.
8. Examples of McMurry macrocyclisations are reviewed in: McMurry, J. E. Chem. Rev. 1989, 89, 1513- 1524; Fürstner, A.; Bogdanovic, B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469; Lectka, T. The McMurry reaction. In: Fürstner, A., editor. Active Metals. Weinheim, VCH, 1996, 85-131. A macrocycle bearing an allylic silyl ether is obtained in: Li, Y.; Li, W.; Li, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2953-2956.
9. Examples of McMurry macrocyclisations are reviewed in: McMurry, J. E. Chem. Rev. 1989, 89, 1513- 1524; Fürstner, A.; Bogdanovic, B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2442-2469; Lectka, T. The McMurry reaction. In: Fürstner, A., editor. Active Metals. Weinheim, VCH, 1996, 85-131. A macrocycle bearing an allylic silyl ether is obtained in: Li, Y.; Li, W.; Li, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2953-2956.
10. Hutchinson, J. H.; Money, T.; Piper, S. E. Can. J. Chem. 1986, 64, 854-860. See also: Clase, J. A.; Money, T. Can. J. Chem. 1992, 70, 1537-1544. In our experience, the reduction of 3,9,10-tribromocamphor into 9,10-dibromocamphor with zinc-acetic acid was best performed at 18 °C.
11. Hutchinson, J. H.; Money, T.; Piper, S. E. Can. J. Chem. 1986, 64, 854-860. See also: Clase, J. A.; Money, T. Can. J. Chem. 1992, 70, 1537-1544. In our experience, the reduction of 3,9,10-tribromocamphor into 9,10-dibromocamphor with zinc-acetic acid was best performed at 18 °C.
12. Rücker, C. Chem. Rev. 1995, 95, 1009-1064.
13. 3). Aldehyde 10: δ 0.89 (s, 3 H); 1.04 (br s, 21 H); 1.27 (m, 1 H); 1.73 (t, J = 7.1 Hz, 1 H); 1.74 (t, J = 6.8 Hz, 1 H); 1.83-1.99 (m, 1 H); 2.21 (ddd, J = 15.4, 10.2, 2.8 Hz, 1 H); 2.22-2.52 (m, 3 H); 2.57 (ddd, J = 15.4, 3.3, 1.4 Hz, 1 H); 3.70 (t, J = 6.9 Hz, 2 H); 4.74 (br t, J = 2.3 Hz, 1 H); 4.91 (br t, J = 2.0 Hz, 1 H); 9.78 (dd, J = 2.8, 1.4 Hz, 1 H). Keto phosphonates 15: δ 1.05 (br s, 21 H); 1.15 (d, J= 6.0 Hz, 3 H); 1.32 and 1.33 (2 t, J = 7.1 Hz, 6 H); 1.34 (dd, J= 17.5, 7.1 Hz, 3 H); 1.60 (br s, 3 H); 2.00 (br q, J = 7.6 Hz, 2 H); 2.25 (br t, J = 7.5 Hz, 2 H); 2.64 (dt, J = 17.2, 7.6 Hz, 1 H); 2.87 (dt, J = 17.2, 7.8 Hz, 1 H); 3.22 (dq, J = 25.0, 7.1 Hz, 1 H); 3.91 (sext., J = 5.8 Hz, 1 H); 4.12 (several q, J = 7.1 Hz, 4 H); 5.13 (br t, J = 6.4 Hz, 1 H).
14. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
15. Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526-5528.
16. Collington, E. W.; Meyers, A. I. J. Org. Chem. 1971, 36, 3044-3045.
17. Grieco, P. A.; Pogonowski, C. S. J. Am. Chem. Soc. 1973, 95, 3071-3072.
18. The ester 18 consisted of more than 95% E isomer (gas chromatography) and was used as it was.
19. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741-743.
20. 1H NMR on the H-13 signal which was at δ 5.67 for 19Z and δ 6.65 for 19E.
21. The stereoselective reduction of the carbonyl group will be addressed later.
22. 3). Keto aldehydes 20: δ 0.96 and 0.97 (2 s, 3 H); 1.04 and 1.05 (2 s, 9 H); 1.21-1.30 (m, 1 H); 1.44 and 1.45 (2 br s, 3 H); 1.51-1.61 (m, 2 H); 1.57 (br s, 3 H); 1.62-1.78 (m, 5 H); 1.94-2.03 (m, 1 H); 2.11 (s, 3 H); 2.18 (br q, J = 7.4 Hz, 2 H); 2.23-2.34 (m, 1 H); 2.38 (t, J = 7.4 Hz, 2 H); 2.40-2.45 (2 dd, J = 15.6, 3.4 Hz, 1 H); 2.41-2.49 (m, 1 H); 2.46-2.51 (2 dd, J = 15.6, 2.4 Hz, 1 H); 3.96 and 3.97 (2 t, J = 7.4 and 7.0 Hz, 1 H); 4.83 and 4.84 (2 t, J = 2.2 Hz, 1 H); 4.90 (br t, J = 7.2 Hz, 1 H); 4.97 and 4.98 (2 t, J = 2.7 Hz, 1 H); 5.00 and 5.02 (2 t, J = 7.0 and 6.5 Hz, 1 H); 7.30-7.44 (m, 6 H); 7.60 (m, 2 H); 7.66 (m, 2 H); 9.67 and 9.68 (2 dd, J = 3.4, 2.4 Hz, 1 H). Ketone 2Z δ 0.92 (s, 3 H); 1.61 (s, 6 H); 1.81 (s, 3 H); 2.07-2.50 (m, 13 H); 3.00 (m, 1 H); 4.65 (t, J = 2.2 Hz, 1 H); 4.78 (br t, J = 6.0 Hz, 1 H); 4.88 (t, J = 2.0 Hz, 1 H); 5.05 (br t, J = 5.4 Hz, 1 H); 6.72 (br t, J = 7.4 Hz, 1 H). Ketone 2E δ 0.92 (s, 3 H); 1.54 (s, 3 H); 1.58 (s, 3 H); 1.73 (s, 3 H); 2.58 (ddd, 7 = 13.0, 7.0, 6.0 Hz, 1 H); 2.73 (dt, J = 13.0, 7.8 Hz, 1 H); 4.78 (t, J = 2.3 Hz, 1 H); 4.91 (t, J = 2.0 Hz, 1 H); 5.02 (br t, J = 5.6 Hz, 1 H); 5.06 (m, 1 H); 6.59 (br t, J = 7.5 Hz, 1 H).
23. Clive, D. L. J.; Murthy, K. S. K.; Wee, A. G. H.; Prasad, J. S.; da Silva, G. V. J.; Majewski, M.; Anderson, P. C.; Evans, C. F.; Haugen, R. D.; Heerze, L. D.; Barrie, J. R. J. Am. Chem. Soc. 1990, 112, 3018-3028.
24. 3 did not allow us to improve our yield.
25. 3 did not allow us to improve our yield.
26. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625-1627.
27. 1H NMR.