765915-08-0Relevant academic research and scientific papers
Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: Formal total synthesis of borrelidin (C3-C11 fragment)
Herber, Christian,Breit, Bernhard
, p. 6684 - 6691 (2008/09/17)
A new iterative strategy for the flexible preparation of any oligodeoxypropionate stereoisomer is presented which relies on an o-DPPB-directed copper mediated allylic substitution employing enantiomerically pure Grignard reagents; the reaction is working with perfect control over all aspects of the reaction selectivity. This key C-C bond-forming step features reversed polarity compared with established enolate alkylation methodology. It thus avoids existing problems of enolate alkylation strategies such as enolate reactivity as well as costs and problems associated with the chiral auxiliary. Practicability of this new method is demonstrated through application in natural product syntheses. Thus, an efficient synthesis of the northern part of the angiogenesis inhibitor borrelidin (28), the deoxypropionate building block 27, could be devised, representing a formal total synthesis.
Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution
Breit, Bernhard,Herber, Christian
, p. 3790 - 3792 (2007/10/03)
Can't have too much of a good thing: A flexible, iterative strategy based on a highly selective copper-mediated allylic substitution makes the preparation of any desired oligo(deoxypropionate) stereoisomer possible (see scheme; RDG = reagent-directing group). This approach differs from the established enolate-alkylation methodology through the reversed polarity of the reaction partners and avoids several problems associated with the latter method.
