Synthesis of 1-oxadecalones via the Lewis acid catalyzed dihydropyrone Diels-Alder reaction

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8750-8753

  Seth, Punit P ^a   Totah, Nancy I ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; DECALIN DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; HYDROLYSIS; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0033550222     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9911746     Document Type: Article

References (14)

1. Sugano, M.; Sato, A.; Iijima, Y.; Oshima, T.; Furuya, K.; Kuwano, H.; Hata, T.; Hanzawa, H. J. Am. Chem. Soc. 1991, 113, 5463.
2. For a synthetic approach to the tricyclic furanochroman core of phomactin A, see: Foote, K. M.; Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 275.
3. Chen, D.; Wang, J.; Totah, N. I. J. Org. Chem. 1999, 64, 1776.
4. The use of Lewis acid catalysis to enhance the reactivity of pyrone derivatives as dienophiles remains largely unexplored. For Lewis acid-catalyzed Diels-Alder reactions of benzopyrones, see: (a) Cremins, P. J.; Saengchantara, S. T.; Wallace, T. W. Tetrahedron 1987, 43, 2293. (b) Ohkata, K.; Kubo, T.; Miyamoto, K.; Ono, M.; Yamamoto, J.; Akiba, K. Heterocycles 1994, 38, 1483. (c) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
5. The use of Lewis acid catalysis to enhance the reactivity of pyrone derivatives as dienophiles remains largely unexplored. For Lewis acid-catalyzed Diels-Alder reactions of benzopyrones, see: (a) Cremins, P. J.; Saengchantara, S. T.; Wallace, T. W. Tetrahedron 1987, 43, 2293. (b) Ohkata, K.; Kubo, T.; Miyamoto, K.; Ono, M.; Yamamoto, J.; Akiba, K. Heterocycles 1994, 38, 1483. (c) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
6. The use of Lewis acid catalysis to enhance the reactivity of pyrone derivatives as dienophiles remains largely unexplored. For Lewis acid-catalyzed Diels-Alder reactions of benzopyrones, see: (a) Cremins, P. J.; Saengchantara, S. T.; Wallace, T. W. Tetrahedron 1987, 43, 2293. (b) Ohkata, K.; Kubo, T.; Miyamoto, K.; Ono, M.; Yamamoto, J.; Akiba, K. Heterocycles 1994, 38, 1483. (c) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
7. In these applications the dihydropyrone dienophile is recovered intact. No other products were isolated from the reaction mixture.
8. Compound 6 is formed as a ca. 8:1 mixture of diastereomers. The stereochemistry of the major product (shown) was determined by NOE studies on the diol 7 and its minor diastereomer.
9. 2.
10. In this case, direct hydrolysis of the enol ether is complicated by the facile degradation of the product 1-oxadecalone. See ref 3.
11. The corresponding pyrone derivatives do react with dienes of this type, although generally in low yields or under forcing conditions. (a) Groundwater, P. W.; Hibbs, D. E.; Hursthouse, M. B.; Nyerges, M. Heterocycles 1996, 43, 745. (b) Hsung, R. P. Heterocycles 1998, 48, 421. See also ref 4c.
12. The corresponding pyrone derivatives do react with dienes of this type, although generally in low yields or under forcing conditions. (a) Groundwater, P. W.; Hibbs, D. E.; Hursthouse, M. B.; Nyerges, M. Heterocycles 1996, 43, 745. (b) Hsung, R. P. Heterocycles 1998, 48, 421. See also ref 4c.
13. 3.
14. 1-Methoxy-1,3-cyclohexadiene is purchased from Aldrich Chemical Co., Inc. and contains approximately 35% of 1-methoxy-1,4-cyclohexadiene.