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Synthesis of the C(1)–C(11) Polyene Fragment of Apoptolidin with a New Sulfur Dioxide‐Based Organic Chemistry
Author(s) -
Bouchez Laure C.,
Vogel Pierre
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500165
Subject(s) - polyene , stereoselectivity , chemistry , sulfur dioxide , sulfur , fragment (logic) , total synthesis , organic synthesis , stereochemistry , organic chemistry , flexibility (engineering) , combinatorial chemistry , catalysis , algorithm , mathematics , statistics
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 ε‐alkanesulfonyl‐γ,δ‐unsaturated ketones. The flexibility and efficiency of this methodology are illustrated by the preparation of (+)‐methyl (2 E ,4 E ,6 E ,8 R ,9 S )‐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.