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 epsilon-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.
Bouchez
Laure C
LC
Laboratory of Glycochemistry and Asymmetric Synthesis, Swiss Federal Institute of Technology (EPFL), Switzerland.
Vogel
Pierre
P
D039903:Actinobacteria / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D017209:Apoptosis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009369:Neoplasms / Q000628:therapy; D051381:Rats; D013458:Sulfur Dioxide / Q000737:chemistry*
D000970:Antineoplastic Agents; D018942:Macrolides; D013458:Sulfur Dioxide; C114125:apoptolidin