Citation: Mansour Nawasreh. Chemo-and regioselective hydroboration of △^14,15 in certain cephalostatin analogue[J]. Chinese Chemical Letters, ;2008, 19(12): 1391-1394. doi: 10.1016/j.cclet.2008.09.055 shu

Chemo-and regioselective hydroboration of △^14,15 in certain cephalostatin analogue

Mansour Nawasreh

Basic Sciences Department, Faculty of Engineering Technology, Al-Balqa Applied University, P. B. 15008, Marka, 11134 Amman, Jordan

Received Date: 16 April 2008

Fund Project: The author would like to acknowledge the Deutsche Forschungsgemeinschaft DFG for funding this work, which carried out in the laboratories of Professor H. Duddeck, Leibniz University of Hannover, to whom the author is very grateful. The author also acknowledges Professor W. Beil for biological evaluation.

The symmetrical diketone Ⅱ, which can be synthesized in gram scale using a well established method, was used as a starting material to prepare the 11a-methoxy ketomethylene Ⅵ. This is in continuation of our study aiming at the synthesis of multi-hydroxylated cephalostatin analogues, as for example cephalostatin 1 Ⅰ, a potent anti-tumor natural product. Compound Ⅵ underwent chemo- and regioselective hydroboration reaction at only one of △^14,15 double bonds furnishing compound Ⅸ as a major product in a fair yield.
- Cephalostatin 1,
- Diketone,
- Hydroboration of △^14,15double bond,
- Anti-cancer activity
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12. [12]
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18. [18]
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19. [19]
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20. [20]
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