Oxidative Intramolecular [4+2]Cycloaddition of o-[(ω-Phenylthioethynyl)acyl]phenols Followed by the Aromatic Pummerer-type Reaction: A Novel Preparation of the peri-Hydroxy Dihydroquinone Structure

Synlett

Volumn 1997, Issue 3, 1997, Pages 310-312

  Akai, Shuji ^a   Iio, Kiyosei ^a   Takeda, Yoshifumi ^a   Ueno, Hiroshi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001251136     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5787     Document Type: Article

References (18)

1. a) Kita, Y.; Okunaka, R.; Honda, T.; Shindo, M.; Tamura, O. Tetrahedron Lett. 1989, 30, 3995-3998;
2. b) Kita, Y.; Okunaka, R.; Honda, T.; Kondo, M.; Tamura, O.; Tamura, Y. Chem. Pharm. Bull. 1991, 39, 2106-2114.
3. We have also reported the preparation of the DEF-ring of fredericamycin A using a similar cycloaddition methodology. See, Kita, Y.; Ueno, H.; Kitagaki, S.; Kobayashi, K.; Iio, K.; Akai, S. J. Chem. Soc., Chem. Commun. 1994, 701-702.
4. a) Akai, S.; Takeda, Y.; Iio, K.; Yoshida, Y.; Kita, Y. J. Chem. Soc., Chem. Commun. 1995, 1013-1014;
5. b) Akai, S.; Iio, K.; Takeda, Y.; Ueno, H.; Yokogawa, K.; Kita, Y. ibid. 1995, 2319-2320;
6. c) Kita, Y.; Takeda, Y.; Iio, K.; Yokogawa, K.; Takahashi, K.; Akai, S. Tetrahedron Lett. 1996, 37, 7545-7548.
7. 2 column chromatography in 50-60% yield.
8. Filippova, A. Kh.; Borisowa, A. I.; Shostakovskii, M. F. Khim. Atsetilena 1968, 64-65 (Chem. Abstr. 1969, 70, 106116c); Laurence, C.; Guillemé, J.; Kirschleger, B. J. Chem. Soc., Perkin Trans. 2 1981, 1341-1343.
9. Filippova, A. Kh.; Borisowa, A. I.; Shostakovskii, M. F. Khim. Atsetilena 1968, 64-65 (Chem. Abstr. 1969, 70, 106116c); Laurence, C.; Guillemé, J.; Kirschleger, B. J. Chem. Soc., Perkin Trans. 2 1981, 1341-1343.
10. Filippova, A. Kh.; Borisowa, A. I.; Shostakovskii, M. F. Khim. Atsetilena 1968, 64-65 (Chem. Abstr. 1969, 70, 106116c); Laurence, C.; Guillemé, J.; Kirschleger, B. J. Chem. Soc., Perkin Trans. 2 1981, 1341-1343.
11. Compounds i-iii were obtained from the condensation reaction of 1 and 3 under various conditions, which were probably formed through the addition of water or p-nitrophenol to initially formed 4 or 3 itself. Further condensation of 1 with iii did not proceed. (Matrix Presented)
12. Difficulties in the preparation of the alkoxypropiolates were also reported. See, a) Gupta, I.; Yates, P. J. Chem. Soc., Chem. Commun. 1982, 1227-1228;
13. b) Camps, F.; Coll, J.; Llebaria, A.; Moretó, J. M.; Ricart, S. Synthesis 1989, 123-124;
14. c) Paquette, L. A.; Wang, T.-Z.; Sivik, M. R. J. Am. Chem. Soc. 1994, 116, 11323-11334.
15. Bromination of terminal acetylenes: See, Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 727-729.
16. 5Si: C, 68.68; H, 6.38; N, 2.86. Found: C, 68.47; H, 6.34; N, 2.83.
17. 1H NMR, HRMS) and/or elemental analyses for the other unknown compounds (11a,b, 12b, 9b, 16, and the corresponding diacetate of 17) were obtained.
18. Comparison of the LUMO energy level for the dienophile model iv, corresponding to 10a, with the unsubstituted v and ethoxy derivatives vi shows the high reactivity of phenylthioacetylene as the dienophile [The energy levels were calculated by Spartan (ver. 3.1.2) using the AM1 Hamiltonian]. (Table Presented)