Total synthesis and absolute stereochemistry of (+)-batzellaside B and its C8-epimer, a new class of piperidine alkaloids from the sponge Batzella sp. |
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| Authors: | Jolanta WierzejskaManami Ohshima Toshiyasu InuzukaTetsuya Sengoku Masaki TakahashiHidemi Yoda |
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| Institution: | a Department of Materials Science, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Naka-ku, Hamamatsu 432-8561, Japan
b Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan |
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| Abstract: | The first total synthesis of (+)-batzellaside B and its C8-epimer was completed from a known l-arabinose-derived tribenzyl ether in 22 steps with overall yields of 3.9% and 5.4%, respectively. The absolute configuration of (+)-batzellaside B was unambiguously determined to be 1S,3S,4S,5R,8S by the Mosher analysis of a synthetic intermediate prepared through a separate route. |
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