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• W2060834694 abstract "The iterative homologation of boronic esters using chiral lithiated benzoate esters and chloromethyllithium has been applied to the highly efficient syntheses of two natural products, (+)-kalkitoxin and (+)-hydroxyphthioceranic acid. The chiral lithiated benzoate esters (>99% ee) were generated from the corresponding stannanes, which themselves were prepared by Hoppe–Beak deprotonation of ethyl 2,4,6-triisopropyl-benzoate with s-BuLi in the presence of (+)- or (−)-sparteine and trapping with Me3SnCl followed by recrystallization. In addition, it was found that purification between several homologations could be avoided, substantially increasing both chemical and manpower efficiency. In the case of (+)-kalkitoxin, six iterative homologations were conducted on commercially available p-MeOC6H4CH2Bpin to build up the core of the molecule before the C–B bond was converted into the desired C–N bond, without purification of intermediates. In the case of (+)-hydroxyphthioceranic acid, 16 iterative homologations w..." @default.
• W2060834694 created "2016-06-24" @default.
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• W2060834694 date "2015-01-27" @default.
• W2060834694 modified "2023-10-02" @default.
• W2060834694 title "Toward Ideality: The Synthesis of (+)-Kalkitoxin and (+)-Hydroxyphthioceranic Acid by Assembly-Line Synthesis" @default.
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• W2060834694 doi "https://doi.org/10.1021/ja512875g" @default.
• W2060834694 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25625684" @default.
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