Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin

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• 作者：Ai Suzuki ; Mai Sasaki ; Tetsuya Nakagishi ; Tsuyoshi Ueda ; Naoyuki Hoshiya ; Jun’ichi Uenishi
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：2248-2251
• 全文大小：437K
• 年卷期：0
• ISSN：1523-7052

文摘

Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C₂₂–C₁₀ threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly.