Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation

Chemistry - A European Journal 2011
Claudia J. Exner, Māris Turks, Freddy Fonquerne, Pierre Vogel

Herein, a major breakthrough in a sulfur dioxide-mediated oxyallylation cascade reaction is reported that allows the preparation of complex long-chain polyketide fragments with more than ten stereogenic centers through a carefully designed desymmetrization process. An allylbissilane is combined, under the appropriate reaction conditions, with two different 1,3-dioxy-1,3-dienes permitting the construction of a 13-membered polypropionate precursor in one pot. Four stereocenters are selectively created during this process. The so-obtained pseudo-C2- or -CS-symmetric products are desymmetrized through selective deprotection and can be selectively elongated in both directions using aldol chemistry.

Keywords
aldol reaction;allylsilanes;asymmetric synthesis;polyketides;sulfur dioxide;tandem reactions
DOI
10.1002/chem.201003264
Hyperlink
http://onlinelibrary.wiley.com/doi/10.1002/chem.201003264/abstract

Exner, C., Turks, M., Fonquerne, F., Vogel, P. Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation. Chemistry - A European Journal, 2011, Vol.17, Iss.15, pp.4246-4253. e-ISSN 1521-3765. ISSN 0947-6539. Available from: doi:10.1002/chem.201003264

Publication language
English (en)