Preparative resolution of 2-methyl-4-hexynic acid for the synthesis of optically active m-phenylene PGI2 derivatives and determination of their absolute configuration

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 2981-2989

  Wakita, Hisanori ^a   Yoshiwara, Hideo ^a   Kitano, Yukishige ^b   Nishiyama, Hisao ^c   Nagase, Hiroshi ^a  

^a TORAY INDUSTRIES INC   (Japan)

^b TORAY RESEARCH CENTER INC   (Japan)

^c TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ANTITHROMBOCYTIC AGENT; BERAPROST; CINCHONIDINE; ILOPROST; PROSTACYCLIN DERIVATIVE; QUININE;

ARTICLE; CRYSTALLIZATION; DIASTEREOISOMER; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; OPTICAL ROTATION; PRIORITY JOURNAL; X RAY ANALYSIS;

EID: 0034725688     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00251-2     Document Type: Article

References (13)

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2. Wakita, H.; Matsumoto, K.; Yoshiwara, H.; Hosono, Y.; Hayashi, R.; Nishiyama, H.; Nagase, H. Tetrahedron 1999, 55, 2449-2474.
3. Only Beraprost is a racemic mixture and its relative configuration is shown with regard to its stereochemistry in Fig. 2. The other compounds are optically active and their absolute configurations are shown in Fig. 2.
4. Ohno, K.; Nagase, H.; Matsumoto, K.; Nishiyama, H.; Nishio, S. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Hayashi, O.; Yamamoto, S., Eds.; Raven Press: New York, 1985; Vol. 15, pp. 279-281.
5. Ohno, K.; Nishiyama, H.; Nagase, H.; Matsumoto, K.; Ishikawa, M. Tetrahedron Lett. 1990, 31, 4489-4492.
6. Nagase, H.; Matsumoto, K.; Yoshiwara, H; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493-4494.
7. Nagase, H.; Matsumoto, K.; Nishiyama, H. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1996, 54, 1055-1066.
8. Harre, M.; Trabandt, J.; Westermann. Liebigs Ann. Chem. 1989, 1081-1083.
9. Skuballa, W.; Schillinger, E.; Sturzebecher, C.; Vorbruggen, H. J. Med. Chem. 1986, 29, 313-315.
10. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1997, 38, 7511-7514.
11. There is a brief description about the resolution of 2-methyl-4-hexynic acid in the following literature, but there is no experimental data and no identification by spectroscopic data for its optical isomers: Skuballa, W.; Vorbruggen, H. In Advances in Prostaglandin, Thromboxane, and Leukotriene Research; Samuelsson, B.; Paoletti, R.; Ramwell, P., Eds.; Raven Press: New York, 1983; Vol. 11, pp. 299-305.
12. Wakita, H.; Yoshiwara, H.; Tajima, A.; Kitano, Y.; Nagase, H. Tetrahedron: Asymmetry 1999, 10, 4099-4105.
13. Wakita, H.; Yoshiwara, H.; Nishiyama, H.; Nagase, H. Heterocycles 2000, 53, 1085-1110.