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Addition of Vinylmetallic Reagents to Chiral 2‐Formyltetrahydrofuran
Author(s) -
LamarianoMerketegi Janire,
Lorente Adriana,
Gil Alejandro,
Albericio Fernando,
Álvarez Mercedes
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402987
Subject(s) - chemistry , polyketide , reagent , molecule , chelation , combinatorial chemistry , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , biosynthesis , enzyme
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.