%0 Journal Article %A Yadav, J. S. %A Boyapelly, Kumaraswamy %A Alugubelli, Sathish Reddy %A Pabbaraja, Srihari %A Vangala, Janakiram R %A Kalivendi, Shasi V %D 2011 %T Stereoselective Total Synthesis of (+)-Oploxyne A, (−)-Oploxyne B, and Their C-10 Epimers and Structure Revision of Natural Oploxyne B %U https://acs.figshare.com/articles/journal_contribution/Stereoselective_Total_Synthesis_of_Oploxyne_A_Oploxyne_B_and_Their_C_10_Epimers_and_Structure_Revision_of_Natural_Oploxyne_B/2662822 %R 10.1021/jo102445h.s001 %2 https://ndownloader.figshare.com/files/4324045 %K prostate cancer cell lines %K oploxyne B %K chiral acetylenic alcohol %K diacetylene alcohols oploxyne %K Natural Oploxyne BThe %X 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. %I ACS Publications