235791-67-0Relevant academic research and scientific papers
Stereocontrolled solution and solid phase enolate alkylations and hydroxylations - Generation of three and four contiguous stereogenic carbon atoms in acyclic systems
Hanessian, Stephen,Ma, Jianguo,Wang, Wengui
, p. 4631 - 4634 (1999)
Potassium enolates of γ-alkoxy-α-methyl pentanoates can be alkylated with allylic and benzylic halides in solution and on solid phase with high 2,3-syn selectivity. Polypropionate units can be constructed on solid phase by a series of stereocontrolled conjugate additions and enolate hydroxylations relying on 1,2-induction.
Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors
Hanessian,Ma,Wang
, p. 10200 - 10206 (2007/10/03)
The macrolide bafilomycin A1 was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A1 via a conventional carbodiimide-mediated Keck-type macrolactonization.
