Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
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DOI：
10.1016/j.ejmech.2010.07.036
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发表时间：
2010-10
影响因子：
6.7
通讯作者：
D. K. Reddy;V. Shekhar;P. Prabhakar;B. Chinna Babu;B. Siddhardha;U. S. N. Murthy;Y. Venkateswarlu
中科院分区：
文献类型：
--
作者：
D. K. Reddy;V. Shekhar;P. Prabhakar;B. Chinna Babu;B. Siddhardha;U. S. N. Murthy;Y. Venkateswarlu
A simple and highly efficient synthetic route has been developed for synthesis of (R)-rugulactone (1a), (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one (1b) and its 4S epimer 1c by employing proline-catalyzed α-aminooxylation, Sharpless epoxidation, Mitsunobu reaction as chirality introuducing steps. The antibacterial and antifungal activity of the compounds 1a, 1b and 1c were evaluated. 1a and 1b showed better antibacterial activity against Pseudomonas aeroginosa (MIC=12.5μg/ml for 1a, 25μg/ml for 1b) Klebsiella pneumonia (MIC=25μg/ml for 1a). Compounds (1a, 1b, 1c) exhibited good to moderate antifungal activity.
