Total Synthesis of Piperhancin B and Isofutoquinol
Year: 2026
Type: preprint
Abstract: We report the first total synthesis of piperhancin B, a natural neolignan exhibiting promising nitric oxide production inhibitory activity. Remarkably, this natural product possesses a highly strained housane structure, which constitutes a huge synthetic challenge. Our synthesis is inspired by the biogenetic hypothesis for this natural product, and involves a key [2+2]-cycloaddition promoted by a photosensitizer. The precursor of this biomimetic step is obtained via an organometallic addition between an alkenyl lithium fragment and a quinone monoacetal, allowing to assemble both propylbenzene units. The power of this approach lies in the possibility of slightly modifying the organometallic fragment in order to reach different structures. This way, the total synthesis of isofutoquinol A was also achieved, and this work paves the way to the synthesis and evaluation of other analogues.
Source: ChemRxiv
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: green
OpenAlex ID: W7169877874