Stereoselective total synthesis of (+)-oploxyne A, (-)-oploxyne B, and their C-10 epimers and structure revision of natural oploxyne B |
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Authors: | Yadav J S Boyapelly Kumaraswamy Alugubelli Sathish Reddy Pabbaraja Srihari Vangala Janakiram R Kalivendi Shasi V |
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Affiliation: | Organic Division-I, Indian Institute of Chemical Technology, CSIR, Hyderabad-500 607, India. yadavpub@iict.res.in |
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Abstract: | The first total synthesis of recently isolated diacetylene alcohols oploxyne A, oploxyne B, and their C-10 epimers was accomplished. The structure of natural oploxyne B has been revised. The key steps involved are base-induced double elimination of a carbohydrate-derived β-alkoxy chloride to generate the chiral acetylenic alcohol and Cadiot-Chodkiewicz cross-coupling reaction. The target compounds displayed potent cytotoxicity against neuroblastoma and prostate cancer cell lines. |
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