1146980-55-3Relevant academic research and scientific papers
A formal synthesis of herboxidiene/GEX1A
Yadav, Jhillu S.,Reddy, G. Madhusudhan,Anjum, S. Rehana,Reddy, B. V. Subba
, p. 4389 - 4397 (2014/07/21)
A formal synthesis of herboxidiene/GEX 1A is described. This approach demonstrates successful application of the Prins cyclization for the construction of the tetrahydropyran core of the target molecule. The chirality of the side chain has been established through the Sharpless asymmetric dihydroxylation and Evan's alkylation. The olefin cross-metathesis was applied to couple both key fragments. Copyright
Highly (E)-selective BF3·Et2O-promoted allylboration of chiral nonracemic α-Substituted allylboronates and analysis of the origin of stereocontrol
Chen, Ming,Roush, William R.
supporting information; experimental part, p. 2706 - 2709 (2010/11/18)
(Figure presented) δ-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF 3·Et2O-promoted allylboration with α-Me-allylboronate 1. The origin of high (E)-selectivity is proposed
Solid-phase synthesis of [5.5]-spiroketals
Sommer, Stefan,Kuehn, Marc,Waldmann, Herbert
supporting information; experimental part, p. 1736 - 1750 (2009/08/14)
An efficient and reliable multi-step synthesis of 251 natural product-like [5.5]-spiroketals on solid supports has been developed. As central key step, a double intramolecular hetero-Michael (DIHMA) reaction to alkynones was applied. The sequence allows for introduction of numerous substituents on the scaffold and for variation of stereochemistry. [5.5]-Spiroketals bearing an additional ketone were obtained in high overall yields. Further diversification was achieved by reduction of the ketone and reductive amination using polymer-supported borohydride, Grignard reaction and conversion to oxime derivatives in the solution phase.
