A convenient synthesis of the Beraprost intermediate: A useful method for introducing a C3 unit at the benzyl position

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3703-3704

  Higuchi, Kazuhiro ^c   Sawada, Kazuyuki ^b   Nambu, Hisanori ^a   Shogaki, Takeshi ^b   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b SAWAI PHARMACEUTICAL CO LTD   (Japan)

^c MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; BERAPROST; DRUG DERIVATIVE; PROSTACYCLIN;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; HECK REACTION; REACTION ANALYSIS; SYNTHESIS;

BENZYL COMPOUNDS; EPOPROSTENOL;

EID: 0142042914     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035371+     Document Type: Article

References (26)

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8. Review: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Nagase, H.; Matsumoto, K.; Nishiyama, H. Yuki Gousei Kagaku Kyoukaishi 1999, 57, 1116. (c) Nishino, S.; Nagase, H.; Kanou, K.; Aoki, S.; Kanabayashi, Y. Yakugaku Zasshi 1997, 117, 509. Synthesis of (±)-Beraprost. (d) Ohno, K. ; Nagase, H.; Matsumoto, K. European Patent EP84,-856, 1983; Chem. Abstr. 1984, 100, 51356m. (e) Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489. (f) Wakita, H.; Matsumoto, K.; Yoshiwara, H.; Hosono, Y.; Hayashi, R.; Nishiyama, H.; Nagase, H. Tetrahedron 1999, 55, 2449. Synthesis of optically active Beraprost. (g) Nagase, H.; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493. (h) Wakita, H.; Yoshiwara, H.; Tajima, A.; Kitano, Y.; Nagase, H. Tetrahedron: Asymmetry 1999, 10, 4099. (i) Wakita, H.; Yoshiwara, H.; Nishiyama, H.; Nagase, H. Heterocycles 2000, 53, 1085. (j) Wakita, H.; Yoshiwara, H.; Kitano, Y.; Nishiyama, H.; Nagase, H. Tetrahedron: Asymmetry 2000, 11, 2981.
9. Review: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Nagase, H.; Matsumoto, K.; Nishiyama, H. Yuki Gousei Kagaku Kyoukaishi 1999, 57, 1116. (c) Nishino, S.; Nagase, H.; Kanou, K.; Aoki, S.; Kanabayashi, Y. Yakugaku Zasshi 1997, 117, 509. Synthesis of (±)-Beraprost. (d) Ohno, K. ; Nagase, H.; Matsumoto, K. European Patent EP84,-856, 1983; Chem. Abstr. 1984, 100, 51356m. (e) Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489. (f) Wakita, H.; Matsumoto, K.; Yoshiwara, H.; Hosono, Y.; Hayashi, R.; Nishiyama, H.; Nagase, H. Tetrahedron 1999, 55, 2449. Synthesis of optically active Beraprost. (g) Nagase, H.; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493. (h) Wakita, H.; Yoshiwara, H.; Tajima, A.; Kitano, Y.; Nagase, H. Tetrahedron: Asymmetry 1999, 10, 4099. (i) Wakita, H.; Yoshiwara, H.; Nishiyama, H.; Nagase, H. Heterocycles 2000, 53, 1085. (j) Wakita, H.; Yoshiwara, H.; Kitano, Y.; Nishiyama, H.; Nagase, H. Tetrahedron: Asymmetry 2000, 11, 2981.
10. Review: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Nagase, H.; Matsumoto, K.; Nishiyama, H. Yuki Gousei Kagaku Kyoukaishi 1999, 57, 1116. (c) Nishino, S.; Nagase, H.; Kanou, K.; Aoki, S.; Kanabayashi, Y. Yakugaku Zasshi 1997, 117, 509. Synthesis of (±)-Beraprost. (d) Ohno, K. ; Nagase, H.; Matsumoto, K. European Patent EP84,-856, 1983; Chem. Abstr. 1984, 100, 51356m. (e) Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489. (f) Wakita, H.; Matsumoto, K.; Yoshiwara, H.; Hosono, Y.; Hayashi, R.; Nishiyama, H.; Nagase, H. Tetrahedron 1999, 55, 2449. Synthesis of optically active Beraprost. (g) Nagase, H.; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493. (h) Wakita, H.; Yoshiwara, H.; Tajima, A.; Kitano, Y.; Nagase, H. Tetrahedron: Asymmetry 1999, 10, 4099. (i) Wakita, H.; Yoshiwara, H.; Nishiyama, H.; Nagase, H. Heterocycles 2000, 53, 1085. (j) Wakita, H.; Yoshiwara, H.; Kitano, Y.; Nishiyama, H.; Nagase, H. Tetrahedron: Asymmetry 2000, 11, 2981.
11. Review: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Nagase, H.; Matsumoto, K.; Nishiyama, H. Yuki Gousei Kagaku Kyoukaishi 1999, 57, 1116. (c) Nishino, S.; Nagase, H.; Kanou, K.; Aoki, S.; Kanabayashi, Y. Yakugaku Zasshi 1997, 117, 509. Synthesis of (±)-Beraprost. (d) Ohno, K. ; Nagase, H.; Matsumoto, K. European Patent EP84,-856, 1983; Chem. Abstr. 1984, 100, 51356m. (e) Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489. (f) Wakita, H.; Matsumoto, K.; Yoshiwara, H.; Hosono, Y.; Hayashi, R.; Nishiyama, H.; Nagase, H. Tetrahedron 1999, 55, 2449. Synthesis of optically active Beraprost. (g) Nagase, H.; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493. (h) Wakita, H.; Yoshiwara, H.; Tajima, A.; Kitano, Y.; Nagase, H. Tetrahedron: Asymmetry 1999, 10, 4099. (i) Wakita, H.; Yoshiwara, H.; Nishiyama, H.; Nagase, H. Heterocycles 2000, 53, 1085. (j) Wakita, H.; Yoshiwara, H.; Kitano, Y.; Nishiyama, H.; Nagase, H. Tetrahedron: Asymmetry 2000, 11, 2981.
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