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(-)-Callystatin A

The potent antitumor polyketide ( - )-callystatin A was isolated in 1997 by Kobayashi and co-workers from the marine sponge Callyspongia truncata. ( - )-Callystatin A shows remarkable high activity (IC 50 = 10 pg/mL) against KB tumor cell lines and 20 pg/mL against L1210 cells. In 1998, the Kobayashi group reported the first total synthesis of callystatin A which was followed by those from Crimmins, Smith, Kalesse, Enders, Marshall, Lautens and Panek. Subsequently, the Kobayashi group reported the preparation of several structural analogues of callystatin A to develop structure-activity relationships.

 

( - )-Callystatin A was isolated in very small amounts (1 mg from 100 Kg of sponge). Attracted by its potent cytotoxicity, and to provide material for more extensive biological evaluation, along with access to promising novel analogues, we have undertaken the total synthesis of callystatin A.



A highly convergent and efficient total synthesis of the potent antitumor polyketide (-)- callystatin A is described. The synthesis required 19 steps from N-propionyl oxazolidinone and produced the desired product in 3.5% overall yield.

 

  1. “Total synthesis of the potent antitumor polyketide (-)-callystatin A”. Dias, L.C. Meira, P.R.R. Journal of Organic Chemistry 2005, 70 , 4763-4773.

 

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