Synthesis of optically active cyclopenta[b]benzofuran as a precursor of m-phenyleneprostacyclin

Synlett

Volumn , Issue 8, 1998, Pages 930-932

  Nishiyama, Hisao ^a   Sakata, Naoya ^a   Sugimoto, Hayato ^a   Motoyama, Yukihiro ^a   Wakita, Hisanori ^b   Nagase, Hiroshi ^b  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b TORAY INDUSTRIES INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000407669     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1819     Document Type: Article

References (20)

1. a) Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489.
2. b) Nagase, H.; Matsumoto, K.; Yoshihara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
3. c) Nishiyama, H.; Isaka, K.; Itoh, K.; Ohno, K.; Nagase, H.; Matsumoto, K.; Yoshihara, H. J. Org. Chem. 1992, 57, 407.
4. d) Nishiyama, H.; Sakata, N.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett 1997, 1147.
5. a) Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253.
6. b) Yoshida, Y.; Sato, Y.; Okamoto, S.; Sato, F. J. Chem. Soc., Chem. Commun. 1995, 811.
7. (+)-3 is available from Fluka (00850); >99% ee.
8. For Mitsunobu reaction with phenol derivatives; see, Paquette, L. A. (editor-in-chief) "Encyclopedia of Reagents for Organic Synthesis"; John Wiley & Sons, New York: 1995, Vol. 8, p. 5382.
9. 3) δ 2.15 (dt, 1H), 3.08 (dt, 1H), 5.23 (bm, 2H), 6.30 (s, 2H), 6.80-7.0 (m, 4H), 7.2-7.35 (m, 4H), 7.55 (d, 1H) ppm.
10. a) Goux, C.; Lhoste, P.; Sinou, D. Synlett 1992, 725. As a review,
11. b) Tsuji, J. Palladium Reagents and Catalysis, Innovations in Organic Synthesis; John Wiley & Sons: Chichester, 1995; p. 61 or p. 290.
12. c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
13. 3) δ 1.71 (d, J = 9.8 Hz, 1H), 1.90 (dt, 1H), 2.83 (m, 1H), 4.72 (m, 1H), 5.14 (m, 1H), 6.20 (m, 2H), 6.85 (t, 1H), 6.96 (d, 1H), 7.25 (t, 1H), 7.55 (d, 1H) ppm.
14. (-)-1: oil; for spectroscopic data, see ref 1c and 1d; optical purity (chiral GC analysis, Astec Chiraldex GT-A), >99%.
15. 3).
16. Nagase, H.; Matsumoto, K.; Nishiyama, H. J. Synth. Org. Chem. Jpn. 1996, 54, 1055; see, scheme 10 and 11. And ref 1b.
17. 3) δ 2.38 (ddd, 1H), 2.75 (ddd, 1H), 5.57 (m, 1H), 5.63 (m, 1H), 6.30 (m, 2H), 6.9-7.0 (m, 3H), 7.30 (d, 1H), 7.68 (s, 2H) ppm.
18. a) Trost, B. M.; Patterson, D. E. J. Org. Chem. 1998, 63, 1339 and references therein.
19. b) Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2396.
20. 2 complex showed almost similar activity. In place of phenol, o-bromophenol was subjected to the reaction giving the corresponding adduct in 53% yield and 91% ee. The dibenzoate derivative in place of the diacetate 12 could be simlarly converted to the correspondig phenoxy adduct in 70% yield and 95% ee.