Synthesis of Neocaesalpin A, AA, and Nominal Neocaesalpin K
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Date
2023-11-27
Publication Type
Journal Article
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yes
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Abstract
The first total synthesis of heavily oxidized cassane-type diterpenoid neocaesalpin A (1) is disclosed. At the heart of the synthesis lies an intermolecular Diels–Alder reaction that rapidly assembles the target framework from commercial materials. A carefully orchestrated sequence of oxidations secured the desired oxygenation pattern. Late-stage release of the characteristic butenolide occurred through a novel mercury(II)-mediated furan oxidation. Successful extension of the route allowed preparation of neocaesalpin AA (2) as well as nominal neocaesalpin K (3) and suggested structural revision of neocaesalpin K, leading to the hypothesis that the two are likely the same natural product with correct assignment as 2.
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published
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Journal / series
Volume
62 (48)
Pages / Article No.
Publisher
Wiley-VCH
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Edition / version
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Date collected
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Subject
Cycloaddition; Natural Products; Structure Elucidation; Total Synthesis
Organisational unit
03511 - Carreira, Erick M. / Carreira, Erick M.
Notes
Funding
189921 - An in silico and chemo-biological approach to identify anti-infective and pro-metabolic natural products (SNF)