Total synthesis of (+)-eupomatilone 2 via asymmetric [2,3]-Wittig rearrangement of highly oxygenated biphenylmethyl ethers |
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Authors: | Yoshimi HirokawaMaria Kitamura Chiharu KatoYuki Kurata Naoyoshi Maezaki |
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Institution: | Faculty of Pharmacy, Osaka Ohtani University, 3-11-1 Nishikiori-Kita, Tondabayashi, Osaka 584-8540, Japan |
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Abstract: | We have achieved the total synthesis of (±)- and (+)-eupomatilone 2 isolated from the Australian shrub Eupomatia bennettii. The key reaction was an asymmetric 2,3]-Wittig rearrangement employing a bis(oxazoline) chiral ligand. Although the highly oxygenated biphenylmethyl ether exhibited considerably lowered enantioselectivity as compared with the non-substituted biphenylmethyl ether, the selectivity was improved to 89% ee by using n-BuLi and ether as the base and the co-solvent, respectively. |
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Keywords: | Asymmetric synthesis Natural product [2 3]-Wittig rearrangement Bis(oxazoline) ligand |
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