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Stereoselective Total Synthesis of (+)-Oploxyne A, (−)-Oploxyne B, and Their C-10 Epimers and Structure Revision of Natural Oploxyne B

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journal contribution
posted on 15.04.2011 by J. S. Yadav, Kumaraswamy Boyapelly, Sathish Reddy Alugubelli, Srihari Pabbaraja, Janakiram R Vangala, Shasi V Kalivendi
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.