Application of Lithiation–Borylation to the Total Synthesis of (−)-Rakicidin F

Christian P. Bold, Kay Yeung, Felix Pape, Daniel Kaiser, Varinder K. Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)
13 Downloads (Pure)


The stereochemistry of the lipophilic side chain of (+)-rakicidin F had not been determined until recently. Using our lithiation–borylation methodology (“assembly line synthesis”) we were able to efficiently prepare the all-syn isomer as well as the C-21 epimer of the side chain, and comparison with the natural product suggested that the natural product had all-syn stereochemistry. Completion of the total synthesis using a macrolactamization of the northern amide enabled us to confirm Wang and Chen’s stereochemical findings for the structure of (+)-rakicidin F.
Original languageEnglish
Pages (from-to)9398-9402
JournalOrganic Letters
Issue number51
Early online date20 Dec 2022
Publication statusPublished - 30 Dec 2022


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