Synthesis of (tetrahydrofuranyl)tetrahydrofurans via radical cyclization of bis(β-alkoxyacrylates)

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 23, 1999, Pages 3395-3396

  Lee, Eun ^a   Song, Ho Young ^a   Kim, Hee Jo ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000158579     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908456h     Document Type: Article

References (16)

1. (a) E. Lee, J. S. Tae, C. Lee and C. M. Park, Tetrahedron Lett., 1993, 34, 4831;
2. (b) E. Lee, J. S. Tae, Y. H. Chong, Y. C. Park, M. Yun and S. Kim, Tetrahedron Lett., 1994, 35, 129;
3. (c) E. Lee and C. M. Park, J. Chem. Soc., Chem. Commun., 1994, 293;
4. (d) E. Lee, J.-w. Jeong and Y. Yu, Tetrahedron Lett., 1997, 38, 7765;
5. (e) E. Lee, C. M. Park and J. S. Yun, J. Am. Chem. Soc., 1995, 117, 8017;
6. (f) E. Lee, S.-K. Yoo, Y.-S. Cho, H.-S. Cheon and Y. H. Chong, Tetrahedron Lett., 1997, 38, 7757.
7. In this case, a small amount of the minor product 4 was also obtained.
8. E. Lee, S.-K. Yoo, H. Choo and H. Y. Song, Tetrahedron Lett., 1998, 39, 317.
9. +, 3), 157 (86), 83 (100).
10. 6 287.1495, found 287.1493.
11. A trace amount of a minor (presumably epimeric) product was obtained.
12. Sharpless asymmetric dihydroxylation of trans-1,6-dibromohex-3-ene, obtained from trans-hex-3-ene-1,6-diol via mesylation and bromide substitution, provided 74% yield of (3R,4R)-1,6-dibromohexane-3,4-diol in high enantiomeric excess (>98%). Reaction of this diol with ethyl propiolate was a little sluggish, and gave 40% yield of the corresponding bis(β-alkoxyacrylate). Radical cyclization produced ethyl ester analogues of 16 and 17 in 72% and 6% yield, respectively.
13. 6 287.1495, found 287.1499.
14. 6 287.1495, found 287.1491.
15. (a) U. Koert, Synthesis, 1995, 115;
16. (b) Many of the more recent references on the synthesis of Annonaceous acetogenins may be found in A. Sinha, S. C. Sinha, S. C. Sinha and E. Keinan, J. Org. Chem., 1999, 64, 2381.