Addition of Vinylmetallic Reagents to Chiral 2-Formyltetrahydrofuran

作者：Lamariano Merketegi Janire; Lorente Adriana; Gil Alejandro; Albericio Fernando; Alvarez Mercedes^*

来源：European Journal of Organic Chemistry, 2015, 2015(1): 235-241.

DOI：10.1002/ejoc.201402987

• Synthetic methods
• Nucleophilic addition
• Natural products
• Oxygen heterocycles
• Allylic compounds

Polyketide macrolides, which belong to an interesting family of metabolites, are complex structures with valuable bioactivity. In this work, several procedures for the bond formation between a vinylorganometallic reagent and a chiral formyl-THF compound were examined for the subsequent application to the total synthesis of phormidolides. Model molecules were synthesized to study and optimize the method that mimics the union of the polyhydroxy chain with the macrocycle of the target polyketide macrolides. A chelation-controlled organometallic addition, a carboalumination, and the Nozaki-Hiyama-Kishi (NHK) reaction were the three chosen reactions to investigate this bond formation. Satisfactory diastereoselectivity and yields were obtained.

• 出版日期2015-1