Stereoselective Construction of 2,7-Disubstituted fused-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (卤)- and (鈭?-Aplysiallene and Their Derivatives

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• 作者：Maki Yamakawa ; Takeshi Kurachi ; Yusuke Yoshikawa ; Mitsuhiro Arisawa ; Yuichiro Okino ; Kuniaki Suzuki ; Hiromichi Fujioka
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：10261-10277
• 全文大小：924K
• ISSN：1520-6904

文摘

A series of trans/trans and cis/cis fused-bis tetrahydrofuran compounds have been obtained stereoselectively in high yields via a one-pot operation involving the intramolecular haloetherification of (Z,Z)-diene diol 19a and (E,E)-diene disilylether 19d, respectively. This method was subsequently applied to the biomimetic-type synthesis of (卤)- and (鈭?-aplysiallene. The inhibitory activities of these compounds and their bromodiene isomers toward Na⁺/K⁺ ATPase were determined in vitro, and gave IC₅₀ values of approximately 15 渭M in all cases.