Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings: A convergent synthesis of diverse benzofuran neolignans

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2279-2282

  Akai, Shuji ^a   Morita, Nobuyoshi ^a   Iio, Kiyosei ^a   Nakamura, Yuka ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; KADSURENONE; LIGAND; LIGNAN; LITHIUM; PHENOL DERIVATIVE; SULFINIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; METABOLISM; SYNTHESIS;

BENZOFURANS; LIGANDS; LIGNANS; LITHIUM; PHENOLS; SULFINIC ACIDS;

EID: 0034720947     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0001261     Document Type: Article

References (32)

1. For reviews, see: Ward, R. S. Nat. Prod. Rep. 1993, 10, 1-28. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183-205. Ward, R. S. Nat. Prod. Rep. 1997, 14, 43-74.
2. For reviews, see: Ward, R. S. Nat. Prod. Rep. 1993, 10, 1-28. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183-205. Ward, R. S. Nat. Prod. Rep. 1997, 14, 43-74.
3. For reviews, see: Ward, R. S. Nat. Prod. Rep. 1993, 10, 1-28. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183-205. Ward, R. S. Nat. Prod. Rep. 1997, 14, 43-74.
4. Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Home, D. A.; Yakushijin, K.; Büchi, G. Tetrahedron Lett. 1999, 40, 5443-5447.
5. Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Home, D. A.; Yakushijin, K.; Büchi, G. Tetrahedron Lett. 1999, 40, 5443-5447.
6. Büchi, G.; Mak, C.-P. J. Am. Chem. Soc. 1977, 99, 8073-8075. Büchi, G.; Chu, P.-S. J. Org. Chem. 1978, 43, 3717-3719. Home, D. A.; Yakushijin, K.; Büchi, G. Tetrahedron Lett. 1999, 40, 5443-5447.
7. (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587.
8. (b) Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970.
9. (c) Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297-9308.
10. Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979-1981. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S J. Org. Chem. 1992, 57, 2135-2143.
11. Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979-1981. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S J. Org. Chem. 1992, 57, 2135-2143.
12. Ponpipom, M. M.; Bugianesi, R. L.; Brooker, D. R.; Yue, B. Z.; Hwang, S. B.; Shen T. Y. J. Med. Chem. 1987, 30, 136-142.
13. (a) Akai, S.; Takeda, Y.; Iio, K.; Yoshida, Y.; Kita, Y. J. Chem. Soc., Chem. Commun. 1995, 1013-1014.
14. (b) Akai, S.; Takeda, Y.; Iio, K.; Takahashi, K.; Fukuda, N.; Kita, Y. J. Org. Chem. 1997, 62, 5526-5536.
15. (c) Kita Y.; Takeda, Y.; Matsugi, M.; Iio, K.; Gotanda, K.; Murata, K.; Akai, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 1529-1531.
16. (d) Kita, Y.; Akai, S.; Fujioka, H. J. Synth. Org. Chem. Jpn. (Special Issue in English) 1998, 56, 963-974.
17. (e) Akai, S.; Kita, Y. Org. Prep. Proc. Int. 1998, 30, 603-629.
18. For related reactions of the p-sulfinylphenol, see: King, R. R. J. Org. Chem. 1978, 43, 3784-3785.
19. For related reactions of the o-sulfinylphenols, see: Jung, M. E.; Kim, C.; von dem Bussche, L. J. Org. Chem. 1994, 59, 3248-3249. Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364.
20. For related reactions of the o-sulfinylphenols, see: Jung, M. E.; Kim, C.; von dem Bussche, L. J. Org. Chem. 1994, 59, 3248-3249. Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364.
21. 2O as an acid anhydride gave 5a in low yields (trace-60%).
22. For reviews, see: Oae, S. Rev. Heteroatom Chem. 1991, 4, 195-225. Satoh, T. J. Synth. Org. Chem. Jpn. 1996, 54, 481-489. Satoh, T. Farumashia 1999, 35, 1225-1229.
23. For reviews, see: Oae, S. Rev. Heteroatom Chem. 1991, 4, 195-225. Satoh, T. J. Synth. Org. Chem. Jpn. 1996, 54, 481-489. Satoh, T. Farumashia 1999, 35, 1225-1229.
24. For reviews, see: Oae, S. Rev. Heteroatom Chem. 1991, 4, 195-225. Satoh, T. J. Synth. Org. Chem. Jpn. 1996, 54, 481-489. Satoh, T. Farumashia 1999, 35, 1225-1229.
25. Little is known about the selectivity of bond fission on unsymmetrical biphenyl sulfoxides, see: Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 2727-2730. Ogawa, S.; Furukawa, N. J. Org. Chem. 1991, 56, 5723-5726. Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341-6348.
26. Little is known about the selectivity of bond fission on unsymmetrical biphenyl sulfoxides, see: Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 2727-2730. Ogawa, S.; Furukawa, N. J. Org. Chem. 1991, 56, 5723-5726. Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341-6348.
27. Little is known about the selectivity of bond fission on unsymmetrical biphenyl sulfoxides, see: Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 2727-2730. Ogawa, S.; Furukawa, N. J. Org. Chem. 1991, 56, 5723-5726. Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341-6348.
28. The selectivity of the breaking bonds a and b was estimated by the ratio of the products, 8 (E = H) and 10, obtained by quenching the reaction mixture of 6 and 9 with MeOH. The use of PhLi (5 equiv) for 6i, 6j, and 6k exclusively provided 8 (E = H) but did not cause any reaction for other sulfoxides. The use of H-BuLi (5 equiv) resulted in moderate ratios (2.2-3.4:1) for 6b, 6g, and 6k and a good ratio (>8:1) for 6i. MeMgBr and PhMgBr brought about no reaction, and t-BuLi caused nonselective formation of the products.
29. 3a
30. For preparation of 3 by direct introduction of the p-sulfinyl groups into the phenols, see: Chasar, D. W.; Pratt, T. M. Phosphorus Sulfur 1978, 5, 35-40. For the indirect preparation of 3, see ref 6b.
31. The sulfinyl group is known as a strong directing group for the ortho-lithiation of aromatic rings, see: Quesnelle, C.; Iihama, T.; Aubert, T.; Perrier, H.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2625-2628 and references therein.
32. A dual use of a sulfinyl group for stereocontrolled C-C bond formation and subsequent regiocontrolled enol generation was reported, see: Posner, G. H.; Hulce, M.; Mallamo, J. P.; Drexler, S. A.; Clardy, J. J. Org. Chem. 1981, 46, 5244-5246.