Total synthesis of (±)-5-deoxystrigol via reductive carbon-carbon bond formation

Journal of Organic Chemistry

Volumn 74, Issue 10, 2009, Pages 3966-3969

  Shoji, Mitsuru ^a   Suzuki, Eriko ^a   Ueda, Minoru ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ATE COMPLEX; CARBON-CARBON BOND FORMATION; CHEMICAL EQUATIONS; REGIOSELECTIVE COUPLING REACTIONS; TOTAL SYNTHESIS;

ACETYLENE; ALUMINA; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CHEMICAL BONDS;

5 DEOXYSTRIGOL; ALKYNE DERIVATIVE; ALUMINUM DERIVATIVE; EPOXIDE; NATURAL PRODUCT; TRANSITION ELEMENT; UNCLASSIFIED DRUG; 5-DEOXYSTRIGOL; CARBON; LACTONE; PHYTOHORMONE;

ARTICLE; CROSS COUPLING REACTION; OLEFINATION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; ENZYME SPECIFICITY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

CARBON; LACTONES; OXIDATION-REDUCTION; PLANT GROWTH REGULATORS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 65949098647     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9002085     Document Type: Article

References (47)

1. Smith, S. E.; Read, D. J. Mycorrhizal Symbiosis; Academic Press: San Diego, 1997.
2. Akiyama, K.; Matsuzaki, K.-I.; Hayashi, H. Nature (London, U.K.) 2005, 435, 824-827.
3. (a) Gomez-Roldan, V.; Fermas, S.; Brewer, P. B.; Puech-Pagès, V.; Dun, E. A.; Pillot, J.-P.; Letisse, F.; Matusova, R.; Danoun, S.; Portais, J.-C.; Bouwmeester, H.; Bécard, G.; Beveridge, C. A.; Rameau, C.; Rochange, S. F. Nature (London, U.K.) 2008, 455, 189-194.
4. (b) Umehara, M.; Hanada, A.; Yoshida, S.; Akiyama, K.; Arite, T.; Takeda-Kamiya, N.; Magome, H.; Kamiya, Y.; Shirasu, K.; Yoneyama, K.; Kyozuka, J.; Yamaguchi, S. Nature (London, U.K.) 2008, 455, 195-200.
5. Strigol: (a) Cook, C. E.; Whichard, L. P.; Turner, B.; Wall, M. E.; Egley, G. H. Science 1966, 154, 1189-1190.
6. Strigyl acetate: (b) Cook, C. E.; Whichard, L. P.; Wall, M. E.; Egley, G. H.; Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Am. Chem. Soc. 1972, 94, 6198-6199
7. Sorgolactone: (c) Hauck, C.; Muller, S.; Schildknecht, H. J. Plant Physiol. 1992, 139, 474-478.
8. Alectrol and orobanchol: (d) Yokota, T.; Sakai, H.; Okuno, K.; Yoneyama, K.; Takeuchi, Y. Phytochemistry 1998, 49, 1967-1973
9. Solgomol: (e) Xie, X.; Yoneyama, K.; Kusumoto, D.; Yamada, Y.; Takeuchi, Y.; Sugimoto, Y.; Yoneyama, K. Tetrahedron Lett. 2008, 49, 2066-2068.
10. Frischmuth, K.; Samson, E.; Kranz, A.; Welzel, P.; Meuer, H.; Sheldrick, W. S. Tetrahedron 1991, 47, 9793-9806.
11. Strigol: (a) MacAlpine, G. A.; Raphael, R. A.; Shaw, A.; Taylor, A. W.; Wild, H.-J. J. Chem. Soc., Perkin Trans. 1 1976, 410-416.
12. (b) Heather, J. B.; Mittal, R. S. D.; Sih, C. J. J. Am. Chem. Soc. 1976, 98, 3661-3669.
13. (c) Brooks, D. W.; Bevinakatti, H. S.; Kennedy, E.; Hathaway, J. J. Org. Chem. 1985, 50, 628-632.
14. (d) Dailey, O. D., Jr. J. Org. Chem. 1987, 52, 1984-1989.
15. (e) Berlage, U.; Schmidt, J.; Peters, U.; Welzel, P. Tetrahedron Lett. 1987, 28, 3091-3094.
16. (f) Samson, E.; Frischmuth, K.; Berlage, U.; Heinz, U.; Hobert, K.; Welzel, P. Tetrahedron 1991, 47, 1411-1416.
17. (g) Hirayama, K; Mori, K. Eur. J. Org. Chem. 1999, 2211-2217.
18. (h) Reizelman, A.; Scheren, M.; Nefkens, G. H. L.; Zwanenburg, B. Synthesis 2000, 1944-1951
19. Sorgolactone: (i) Sugimoto, Y.; Wigchert, S. C. M.; Thuring, J. W. J. F.; Zwanenburg, B. J. Org. Chem. 1998, 63, 1259-1267.
20. (j) Matsui, J.; Bando, M.; Kido, M.; Takeuchi, Y.; Mori, K. Eur. J. Org. Chem. 1999, 2183-2194
21. Orobanchol: (k) Matsui, J.; Yokota, T.; Bando, M.; Takeuchi, Y.; Mori, K. Eur. J. Org. Chem. 1999, 2201-2210.
22. (l) Hirayama, K.; Mori, K. Eur. J. Org. Chem. 1999, 2211-2217.
23. Ogura, K. J. Synth. Org. Chem., Jpn. 1975, 33, 256-269.
24. (a) Biosynthesis of strigolactones via a C40 carotenoid is also revealed: Akiyama, K.; Hayashi, H. New Phytol. 2008, 178, 695-698.
25. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505-5507.
26. (a) Zhao, H.; Pagenkopf, B. L. Chem. Commun. 2003, 2592-2593.
27. (b) Zhao, H.; Engers, D. W.; Morales, C. L.; Pagenkopf, B. L. Tetrahedron 2007, 63, 8774-8780.
28. Anelli, P. L.; Montanari, F.; Quici, S. Organic Synthesis; Wiley: New York, 1993; Coll. Vol.8, p 367.
29. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
30. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
31. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
32. Arbez-Gindre, C.; Berl, V.; Lepointtevin, J.-P. Steroids 2003, 68, 361-365.
33. Lenoir, D. Synthesis 1977, 553-554.
34. (a) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041-1044.
35. (b) Takeshita, H.; Mori, A.; Nakamura, S. Bull. Chem. Soc. Jpn. 1984, 57, 3152-3155.
36. (c) Mukaiyama, T.; Kagayama, A.; Shiina, I. Chem. Lett. 1998, 1107-1108.
37. (a) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 1999, 40, 2811-2814.
38. (b) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717-1720.
39. Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900-6901.
40. Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412-8413.
41. Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1973, 46, 2248-2249.
42. Olefination of diol 21 under the same reaction condition also provided 2.
43. (a) Lohray, B. B. Synthesis 1992, 1035-1052.
44. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2515.
45. (a) Hanessian, S.; Girard, C.; Chiara, J. L. Tetrahedron Lett. 1992, 33, 573-576.
46. (b) Markó, I. E.; Murphy, F.; Kumps, L.; Ates, A.; Touillaux, R.; Craig, D.; Carballares, S.; Dolan, S. Tetrahedron 2001, 57, 2609-2619.
47. f value is 0.50 for 1 and 0.45 for its C2′-epimer.