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Dictyostatin and Its Analogs

Dictyostatin Maria
Maria Jiménez


The synthesis of various analogs of the marine natural product dictyostatin have been of great interest in our laboratory. Dictyostatin is a 22-membered macrolactone isolated in 1994 by Pettit and coworkers from the marine sponge Spongia sp.

Sponge

It inhibits the growth of a variety of cancer cell lines at the low nanomolar range. Since its isolation, structure elucidation and biological activity came to light, we have synthesized a number of analogs in our laboratory in order to gain more insight regarding structure-activity relationships (SAR) studies. We aim to develop a practical, more convergent and higher yielding route to easily access dictyostatin and its simplified analogs.

Analogs

Reference for isolation:

Pettit, G. A.; Cichacz, Z. A.; Gao., F.; Boyd, M. R.; Schmidt, J. M. J. Chem. Soc., Chem Commun. 1994, 1111-1112.

Reference for re-isolation:

Isbrucker, R. A.; Cummins, J.; Pomponi, S. A.; Longley. R. E.; Wright, A. E. Biochem. Pharmacol. 2003, 66, 75-82.

References for Dictyostatin total syntheses

1. Shin, Y.; Fournier, J-H.; Fukui, Y.; Brýckner, A. M.; Curran, D. P. Angew. Chem. Int. Ed. 2004, 43, 4634-4637.
2. Paterson, I.; Britton, R.; Delgado, O.; Meyer, A.; Poullennec, K. G. Angew. Chem. Int. Ed. 2004, 43, 4629-4633.
3. O'Neil, G. W.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 5340.
4. Ramachandran, P. V.; Srivastava, A.; Hazra, D. Org. Lett. 2007, 9, 157-160.