Synthesis of 5,6,7-trinor-4,8-inter-m-phenylene PGI2 and Beraprost

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2449-2474

  Wakita, Hisanori ^a   Matsumoto, Kazuhisa ^a   Yoshiwara, Hideo ^a   Hosono, Yutaka ^a   Hayashi, Ryoji ^a   Nishiyama, Hisao ^b   Nagase, Hiroshi ^a  

^a TORAY INDUSTRIES INC   (Japan)

^b TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BERAPROST; PROSTACYCLIN DERIVATIVE; PROSTAGLANDIN;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; METAL BINDING; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033605189     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00020-4     Document Type: Article

References (39)

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10. (a) Ohno, K.; Nagase, H.; Matsumoto, K.; Nishiyama, H.; Nishio, S. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research ; Vol. 15 eds. Hayashi, O; Yamamoto, S., Eds.; Ravan Press: New York, 1985; pp. 279-281. (b) Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489-4492. (c) Nagase, H.; Matsumoto, K.; Yoshiwara, H.; Tajima, A; Ohno, K. Ibid. 1990, 31, 4493-4494. (d) Nagase, H.; Matsumoto, K.; Nishiyama, H. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1996, 54, 1055-1066.
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14. 2 gave the desired benzofuran derivative (5a) as minor product and the isomer as major product (Hosokawa, T.; Miyagi, S.; Murahashi, S.; Sonoda, A. J. Org. Chem.1978, 43, 2752-2757). (equation presented) Scheme 9. another route of cyclopenta[b]benzofuran (5a) (equation presented) Scheme 10. Another plan of dihydro-3H-cyclopenta[b]benzofuran derivative (5a)
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19. The syntheses of cyclopenta[b]benzofuran derivatives by using Pd(0) or radical cyclization have recently been reported, see: (a) Larock, R. C.; Lee, N. H., US patent, US 5169959, 1992 (Chem. Abstr., 1993, 118, 233757x). (b) Larock, R. C.; Lee, N. H., US patent, US 5233059, 1993 (Chem. Abstr., 1994, 120, 30609u). (c) Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253-6254.
20. The syntheses of cyclopenta[b]benzofuran derivatives by using Pd(0) or radical cyclization have recently been reported, see: (a) Larock, R. C.; Lee, N. H., US patent, US 5169959, 1992 (Chem. Abstr., 1993, 118, 233757x). (b) Larock, R. C.; Lee, N. H., US patent, US 5233059, 1993 (Chem. Abstr., 1994, 120, 30609u). (c) Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253-6254.
21. The syntheses of cyclopenta[b]benzofuran derivatives by using Pd(0) or radical cyclization have recently been reported, see: (a) Larock, R. C.; Lee, N. H., US patent, US 5169959, 1992 (Chem. Abstr., 1993, 118, 233757x). (b) Larock, R. C.; Lee, N. H., US patent, US 5233059, 1993 (Chem. Abstr., 1994, 120, 30609u). (c) Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253-6254.
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38. Absolute configuration of Beraprost (2) was determined by X ray analysis of 64 and 65. The stereoselective syntheses of 64 and 65 will be reported in due course. (equation presented) Scheme 11. Beraprost derivatives, whose absolute configurations were determined
39. The authors thank Dr. Shintaro Nishio at Basic Research Laboratories for pharmacological assays of the synthesized compounds (Nishio, S.; Matsuura, H.; Kanai, N.; Fukatsu, Y; Hirano, T.; Nishikawa, N.; Kameoka, K.; Umetsu, T. Jpn. J. Pharmacol. 1988, 47, 1-10).