Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Convergent Total Synthesis of Paecilomycin B and 6′-epi-Paecilomycin B by a Barbier-Type Reaction Using 2,4,6-Triisopropylphenyllithium

Convergent Total Synthesis of Paecilomycin B and 6′-epi-Paecilomycin B by a Barbier-Type Reaction Using 2,4,6-Triisopropylphenyllithium
Masaya Nakata, Kiyomi Ohba
The convergent total synthesis of the natural product paecilomycin B and its 6′-epimer was investigated. The aryl-C-glycoside skeleton was constructed by an intramolecular Barbier-type reaction using 2,4,6-triisopropylphenyllithium and subsequent deoxygenation of the resulting anomeric hydroxy group. Starting from aryl iodide 24, the addition reaction afforded the thermodynamically stable C-β macrocyclic adduct 41a in 29% yield and the C-α adduct 41b in 1% yield. Meanwhile, aryl iodide 43 (6′-epimer of 24) gave only the C-α adduct 44 in 76% yield. The stereoselectivities of these nucleophilic addition reactions are also discussed.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b03041

DOI: 10.1021/acs.joc.7b03041

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