765915-18-2Relevant academic research and scientific papers
Prediction and determination of the stereochemistry of the 1,3,5-trimethyl-substituted alkyl chain in verucopeptin, a microbial metabolite
Yoshimura, Aya,Kishimoto, Shinji,Nishimura, Shinichi,Otsuka, Saori,Sakai, Yuki,Hattori, Akira,Kakeya, Hideaki
, p. 6858 - 6867 (2014/08/18)
For the prediction of the relative stereochemistry of 1,3-dimethyl substitution in alkyl chains, a simple approach based on 1H NMR data was recently proposed; Δδ values of methylene protons located between methyl-substituted methine carbons can
Stereoselective synthesis of a model C(18)-C(35) spiroketal fragment of integramycin
Sun, Huikai,Abbott, Jason R.,Roush, William R.
, p. 2734 - 2737 (2011/07/30)
A highly stereoselective synthesis of a model C(18)-C(35) spiroketal unit (7) of integramycin has been accomplished via an enantioselective stannyl-crotylboration reaction and an N-iodosuccinimide-mediated spiroketalization of 19a.
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.
