Synthetic studies toward potent cytotoxic agents amphidinolides: Synthesis of the C1-C6 and C9-C17 moieties of amphidinolides O and P

Chemistry Letters

Volumn , Issue 1, 2000, Pages 80-81

  Chakraborty, T K ^a   Das, Sanjib ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034340857     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.80     Document Type: Article

References (15)

1. M. Ishibashi and J. Kobayashi, Heterocycles, 44, 543 (1997).
2. J. Kobayashi and M. Ishihashi, Chem. Rev., 93, 1753 (1993).
3. M. Ishibashi, M. Takahashi, and J, Kohayashi. J. Org. Chem., 60, 6062 (1995).
4. T. K. Chakraborty and S. Dutta, J. Chem. Soc., Perkin Trans. 1, 1997. 1257.
5. B. B. Snider and J. V. Duncia, J. Org. Chem., 45, 3461 (1980).
6. (a) Y. Gan, R. M. Hansun, J. M. Klunder, S. Y. Ko, H. Masamune. and K. B. Sharpless. J. Am. Chem. Soc., 109, 5765 (1987):
7. (b) T. Katsuki and V. S. Martin. Org. React., 48, 1 (1996);
8. Sharpless kinetic resolution of a similar substrate is reported: A. R. Chamberlin, M. Dezube. S. H. Reich, and D. J. Sall. J. Am. Chem. Soc., 111, 6247 (1989):
9. 3CHOH).
10. The stereochemistry of 15 and its minor diastereonier were determined. as described earlier (ret. 4). by converting them to 6-membered acetonides and studying their proton coupling constants (4-5 Hz for syn-protons and 8-9 Hz for anti-protons).
11. K. S. Kim, Y. S. Song, B. H. Lee, and C. S. Hahn, J. Org. Chem., 51, 404 (1986).
12. K. Ishihara, H. Kurihara, and H. Yamamoto, J. Org. Chem., 58, 3791 (1993).
13. -+Na).
14. 2 - nBuLi (Li-phosphonate addition to the ester to give the ketophosphonate).
15. +-H).