A highly efficient synthesis of (-)-PI-091 construction of the 4-alkoxy-2-butene-4-lactam skeleton from Fischer-type carbene complexes, alkynyllithiums, and tosyl isocyanate

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 1918-1919

  Iwasawa, Nobuharu ^a   Maeyama, Katsuya ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITHROMBOCYTIC AGENT; LACTAM DERIVATIVE; PI 091; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030922433     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9700686     Document Type: Article

References (21)

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6. Iwasawa, N.; Maeyama, K.; Saitou, M. J. Am. Chem. Soc. 1997, 119, 1486.
7. For examples of the reactions of transition metal propargyl metallic species with tosyl isocyanate: (a) Giering, W. P.; Raghu, S.; Rosenblum, M.; Cutler, A.; Ehntholt, D.; Fish, R. W. J. Am. Chem. Soc. 1972, 94, 8251. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (d) Shuchart, C. E.; Willis, R. R.; Wojcicki, A. J. Organomet. Chem. 1992, 424, 185. (e) Welker, M. E. Chem. Rev. 1992, 92, 97.
8. For examples of the reactions of transition metal propargyl metallic species with tosyl isocyanate: (a) Giering, W. P.; Raghu, S.; Rosenblum, M.; Cutler, A.; Ehntholt, D.; Fish, R. W. J. Am. Chem. Soc. 1972, 94, 8251. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (d) Shuchart, C. E.; Willis, R. R.; Wojcicki, A. J. Organomet. Chem. 1992, 424, 185. (e) Welker, M. E. Chem. Rev. 1992, 92, 97.
9. For examples of the reactions of transition metal propargyl metallic species with tosyl isocyanate: (a) Giering, W. P.; Raghu, S.; Rosenblum, M.; Cutler, A.; Ehntholt, D.; Fish, R. W. J. Am. Chem. Soc. 1972, 94, 8251. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (d) Shuchart, C. E.; Willis, R. R.; Wojcicki, A. J. Organomet. Chem. 1992, 424, 185. (e) Welker, M. E. Chem. Rev. 1992, 92, 97.
10. For examples of the reactions of transition metal propargyl metallic species with tosyl isocyanate: (a) Giering, W. P.; Raghu, S.; Rosenblum, M.; Cutler, A.; Ehntholt, D.; Fish, R. W. J. Am. Chem. Soc. 1972, 94, 8251. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (d) Shuchart, C. E.; Willis, R. R.; Wojcicki, A. J. Organomet. Chem. 1992, 424, 185. (e) Welker, M. E. Chem. Rev. 1992, 92, 97.
11. For examples of the reactions of transition metal propargyl metallic species with tosyl isocyanate: (a) Giering, W. P.; Raghu, S.; Rosenblum, M.; Cutler, A.; Ehntholt, D.; Fish, R. W. J. Am. Chem. Soc. 1972, 94, 8251. (b) Raghu, S.; Rosenblum, M. J. Am. Chem. Soc. 1973, 95, 3060. (c) Bell, P. B.; Wojcicki, A. Inorg. Chem. 1981, 20, 1585. (d) Shuchart, C. E.; Willis, R. R.; Wojcicki, A. J. Organomet. Chem. 1992, 424, 185. (e) Welker, M. E. Chem. Rev. 1992, 92, 97.
12. We have not yet succeeded in isolating this intermediate.
13. No isomerization of O-cyclized product 2a to N-cyclized product 3a was observed under these conditions (trifiuoroacetic acid in THF at rt).
14. 4. After removal of the solvent, the residue was purified using preparative TLC (hexane:ethyl acetate = 6:4), yielding the corresponding W-cyclized product 3.
15. (a) Shiraki, R.; Sumino, A.; Tadano, K.; Ogawa, S. Tetrahedron Lett. 1995, 36, 5551.
16. (b) Shiraki, R.; Sumino, A.; Tadano, K.; Ogawa, S. J. Org. Chem. 1996, 61, 2845.
17. Rand, C. L.; Van Horn, D. E.; Moore, M. W.; Negishi, E. J. Org. Chem. 1981, 46, 4093.
18. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
19. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.; Kwong, H.; Morikawa, K.; Wang, Z.; Xu, D.; Zhang, X. J. Org. Chem. 1992, 57, 2768.
20. Diastereomers arise from configuration at the N,O-acetal carbon. The relative stereochemistries of 8a and 8b were not determined.
21. Although natural PI-091 is a mixture of diastereomers, both 10a and 10b show nearly the same optical rotation as the natural product.