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

ABSTRACT: 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.

SUBMITTER: Bold CP

PROVIDER: S-EPMC9806854 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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

Bold Christian P CP Yeung Kay K Pape Felix F Kaiser Daniel D Aggarwal Varinder K VK

Organic letters 20221220 51

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 C ...[more]

PMID: 36538642

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