An efficient strategy for the iterative synthesis of a trans-fused polytetrahydropyran ring system via SmI2-induced reductive intramolecular cyclization

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2811-2814

  Hori, Nobuyuki ^a   Matsukura, Hiroko ^a   Matsuo, Goh ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Cyclization; Radical reaction; Samarium diiodide; Tetrahydropyrans

Indexed keywords

TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0033515858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00301-9     Document Type: Article

References (44)

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21. 2-induced reductive cross-couplings and intramolecular cyclizations of carbonyl compounds and α,β-unsaturated esters were reported. For cross-couplings, see: Otsubo K, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986; 27: 5763. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Chem. Commun. 1986; 624. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Perkin Trans. I 1988; 1669. Kawatsura M, Matsuda F, Shirahama H. J. Org. Chem. 1994; 59: 6900. Kawatsura M, Dekura F, Shirahama H, Matsuda F. Synlett 1996; 373. For intramolecular cyclizations, see: Enholm EJ, Trivellas A. Tetrahedron Lett. 1989; 30: 1063. Enholm EJ, Trivellas A. J. Am. Chem. Soc. 1989; 111: 6463. Kito M, Sakai T, Yamada K, Matsuda F, Shirahama H. Synlett 1993; 158. Kito M, Sakai T, Haruta N, Shirahama H, Matsuda F. Synlett 1996; 1057.
22. 2-induced reductive cross-couplings and intramolecular cyclizations of carbonyl compounds and α,β-unsaturated esters were reported. For cross-couplings, see: Otsubo K, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986; 27: 5763. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Chem. Commun. 1986; 624. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Perkin Trans. I 1988; 1669. Kawatsura M, Matsuda F, Shirahama H. J. Org. Chem. 1994; 59: 6900. Kawatsura M, Dekura F, Shirahama H, Matsuda F. Synlett 1996; 373. For intramolecular cyclizations, see: Enholm EJ, Trivellas A. Tetrahedron Lett. 1989; 30: 1063. Enholm EJ, Trivellas A. J. Am. Chem. Soc. 1989; 111: 6463. Kito M, Sakai T, Yamada K, Matsuda F, Shirahama H. Synlett 1993; 158. Kito M, Sakai T, Haruta N, Shirahama H, Matsuda F. Synlett 1996; 1057.
23. 2-induced reductive cross-couplings and intramolecular cyclizations of carbonyl compounds and α,β-unsaturated esters were reported. For cross-couplings, see: Otsubo K, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986; 27: 5763. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Chem. Commun. 1986; 624. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Perkin Trans. I 1988; 1669. Kawatsura M, Matsuda F, Shirahama H. J. Org. Chem. 1994; 59: 6900. Kawatsura M, Dekura F, Shirahama H, Matsuda F. Synlett 1996; 373. For intramolecular cyclizations, see: Enholm EJ, Trivellas A. Tetrahedron Lett. 1989; 30: 1063. Enholm EJ, Trivellas A. J. Am. Chem. Soc. 1989; 111: 6463. Kito M, Sakai T, Yamada K, Matsuda F, Shirahama H. Synlett 1993; 158. Kito M, Sakai T, Haruta N, Shirahama H, Matsuda F. Synlett 1996; 1057.
24. 2-induced reductive cross-couplings and intramolecular cyclizations of carbonyl compounds and α,β-unsaturated esters were reported. For cross-couplings, see: Otsubo K, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986; 27: 5763. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Chem. Commun. 1986; 624. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Perkin Trans. I 1988; 1669. Kawatsura M, Matsuda F, Shirahama H. J. Org. Chem. 1994; 59: 6900. Kawatsura M, Dekura F, Shirahama H, Matsuda F. Synlett 1996; 373. For intramolecular cyclizations, see: Enholm EJ, Trivellas A. Tetrahedron Lett. 1989; 30: 1063. Enholm EJ, Trivellas A. J. Am. Chem. Soc. 1989; 111: 6463. Kito M, Sakai T, Yamada K, Matsuda F, Shirahama H. Synlett 1993; 158. Kito M, Sakai T, Haruta N, Shirahama H, Matsuda F. Synlett 1996; 1057.
25. 2-induced reductive cross-couplings and intramolecular cyclizations of carbonyl compounds and α,β-unsaturated esters were reported. For cross-couplings, see: Otsubo K, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986; 27: 5763. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Chem. Commun. 1986; 624. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Perkin Trans. I 1988; 1669. Kawatsura M, Matsuda F, Shirahama H. J. Org. Chem. 1994; 59: 6900. Kawatsura M, Dekura F, Shirahama H, Matsuda F. Synlett 1996; 373. For intramolecular cyclizations, see: Enholm EJ, Trivellas A. Tetrahedron Lett. 1989; 30: 1063. Enholm EJ, Trivellas A. J. Am. Chem. Soc. 1989; 111: 6463. Kito M, Sakai T, Yamada K, Matsuda F, Shirahama H. Synlett 1993; 158. Kito M, Sakai T, Haruta N, Shirahama H, Matsuda F. Synlett 1996; 1057.
26. 2-induced reductive cross-couplings and intramolecular cyclizations of carbonyl compounds and α,β-unsaturated esters were reported. For cross-couplings, see: Otsubo K, Inanaga J, Yamaguchi M. Tetrahedron Lett. 1986; 27: 5763. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Chem. Commun. 1986; 624. Fukuzawa S, Nakanishi A, Fujinami T, Sakai S. J. Chem. Soc. Perkin Trans. I 1988; 1669. Kawatsura M, Matsuda F, Shirahama H. J. Org. Chem. 1994; 59: 6900. Kawatsura M, Dekura F, Shirahama H, Matsuda F. Synlett 1996; 373. For intramolecular cyclizations, see: Enholm EJ, Trivellas A. Tetrahedron Lett. 1989; 30: 1063. Enholm EJ, Trivellas A. J. Am. Chem. Soc. 1989; 111: 6463. Kito M, Sakai T, Yamada K, Matsuda F, Shirahama H. Synlett 1993; 158. Kito M, Sakai T, Haruta N, Shirahama H, Matsuda F. Synlett 1996; 1057.
27. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
28. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
29. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
30. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
31. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
32. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
33. For other radical-mediated cyclizations using β-alkoxyacrylate as a radical acceptor, see: Araki Y, Endo T, Arai Y, Tanji M, Ishido Y. Tetrahedron Lett. 1989; 30: 2829. Lee E, Tae JS, Lee C, Park CM. Tetrahedron Lett. 1993; 34: 4831. Lee E, Park CM, Yun JS. J. Am. Chem. Soc. 1995; 117: 8017. Yusa Y, Sato W, Shibuya S. Synth. Commun. 1997; 27: 573. Lee E, Yoo SI, Cho YS, Cheon HS, Chong YH. Tetrahedron Lett. 1997; 38: 7757. Lee E, Jeong JW, Yu Y. Tetrahedron Lett. 1997; 38: 7765. Sasaki M, Inoue M, Noguchi T, Takeichi A, Tachibana K. Tetrahedron Lett. 1998; 39: 2783. See also: ref 3g-i.
34. 4NF, THF, rt (75% for 2 steps).
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42. 3SnH in the presence of AIBN in benzene at reflux was reported [3g]; however, the reaction afforded a 24:76 mixture of trans-4 and its cis-isomer (γ-lactone) as the cyclized products.
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44. The use of MeOD instead of MeOH in the present reaction resulted in deuteration at the α-position of the ester.