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.
Keywords: Diels-Alder reactions ; natural products ; polyenes ; Ramberg-Backlund ; reactions ; total synthesis ; Ramberg-backlund reaction ; stereoselective-synthesis ; building-blocks ; polyfunctional sulfones ; 4-component synthesis ; asymmetric-synthesis ; carbonyl-compounds ; transformed-cells ; apoptosis inducer ; one-pot
Ecole Polytech Fed Lausanne, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08