Bouchez, L. C.Vogel, P.2005-11-092005-11-092005-11-09200510.1002/chem.200500165https://infoscience.epfl.ch/handle/20.500.14299/219843WOS:0002313242000047205A 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.Diels-Alder reactionsnatural productspolyenesRamberg-Backlundreactionstotal synthesisRamberg-backlund reactionstereoselective-synthesisbuilding-blockspolyfunctional sulfones4-component synthesisasymmetric-synthesiscarbonyl-compoundstransformed-cellsapoptosis inducerone-pottext::journal::journal article::research article