Synthesis of the C(1)-C(11) polyene fragment of apoptolidin with a new sulfur dioxide-based organic chemistry

A new sulfur dioxide-based organic chemistry has been developed as a novel approach for the stereoselective synthesis of polyene fragments based on our one-pot, four-component synthesis of polyfunctional alpha-alkanesulfonyl-gamma,delta-unsaturated ketones. The flexibility and efficiency of this methodology are illustrated by the preparation of (+)-methyl (2E,4E,6E,8R,9S)-9-([(tert-butyl)dimethylsilyl]oxy}-2,4,6,8- tetramethyl-11-(triethylsilyl)undeca-2,4,6-trien-10-ynoate, a synthetic intermediate of Nicolaou and co-workers, that corresponds to the C(1)-C(11) fragment of apoptolidin, which was used by the authors in their total synthesis of this promising anticancer agent.


Published in:
Chemistry-a European Journal, 11, 16, 4609-4620
Year:
2005
ISSN:
0947-6539
Keywords:
Note:
Ecole Polytech Fed Lausanne, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland.
Other identifiers:
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)