913730-80-0Relevant academic research and scientific papers
Chemoenzymatic synthesis of the C3-C11-fragment of borrelidin
Theurer, Matthias,El Baz, Yana,Koschorreck, Katja,Urlacher, Vlada B.,Rauhut, Guntram,Baro, Angelika,Laschat, Sabine
, p. 4241 - 4249 (2011/09/16)
The ex-chiral pool synthesis of the Theodorakis C3-C11 fragment of borrelidin (1) by a chemoenzymatic approach in nine steps and 12% overall yield starting from enantiopure methyl-branched preen gland wax esters is described. In the initial reaction, the
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.
