Stereocontrolled Total Synthesis of (±)-Saframycin B

Journal of the American Chemical Society

Volumn 104, Issue 18, 1982, Pages 4957-4958

  Fukuyama, Tohru ^a   Sachleben, Richard A ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000771442     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00382a042     Document Type: Article

References (12)

1. Arai, T.; Takahashi, K.; Kubo, A. J. Antibiot. 1977, 30, 1015.
2. Arai, T.; Takahashi, K.; Ishiguro, K.; Mikami, T. Gann 1980, 71, 790.
3. Arai, T.; Takahashi, K.; Kubo, A.; Nakahara, S.; Sato, S.; Aiba, K.; Tamura, C. Tetrahedron Lett. 1979, 2355.
4. Renieramycins, structurally similar to saframycins, have been recently isolated from a marine sponge: Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265.
5. Godfrey, I. M.; Sargent, M. V.; Elix, J. A. J. Chem. Soc., Perkin Trans. 1 1974, 1353.
6. For a review of chemistry of α-metalated isocyanides, see: (a) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 339.
7. Hoppe, D. A. Angew. Chem., Int. 1974, 13, 789.
8. 3H, THF, room temperature; (2) HCOOH, 60°C]: Gallina, C.; Liberatori, A. Tetrahedron 1974, 30, 667.
9. Similar type of reactions has been used for construction of the basic skeleton of pavinan alkaloids: Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601 and references cited therein.
10. Kametani, T. “The Total Synthesis of Natural Products”; ApSimon, J., Ed.; Wiley-Interscience: New York, 1977; Vol. III, pp 47–49.
11. Luly, J. R.; Rapoport, H. J. Org. Chem. 1981, 46, 2745.
12. Jacob, P., III; Callery, P. S.; Shulgin, A. T.; Castagnoli, N., Jr. J. Org. Chem. 1976, 41, 3627.