Stereoselective Total Synthesis of (+)-Oploxyne A, (−)-Oploxyne B, and Their C-10 Epimers and Structure Revision of Natural Oploxyne B
2011-04-15T00:00:00Z (GMT) by
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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