Total Synthesis of Piperhancin B and Isofutoquinol
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.
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BibTeX
@misc{benbouziyane2026total,
title = {{Total Synthesis of Piperhancin B and Isofutoquinol}},
author = {Camil Benbouziyane and Régis Guillot and Cyrille Kouklovsky and Aurélien de la Torre},
howpublished = {HAL},
year = {2026},
month = jul,
doi = {10.26434/chemrxiv.15006385/v1},
url = {https://hal.science/hal-05789004v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Total Synthesis of Piperhancin B and Isofutoquinol
AU - Camil Benbouziyane
AU - Régis Guillot
AU - Cyrille Kouklovsky
AU - Aurélien de la Torre
PY - 2026
DA - 2026/07/21
PB - HAL
DO - 10.26434/chemrxiv.15006385/v1
UR - https://hal.science/hal-05789004v1
AB - 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.
ER -