Total Syntheses of Natural Tubelactomicins B, D, and E: Establishment of Their Stereochemistries

详细信息    查看全文

• 作者：Kiyoto Sawamura ; Keigo Yoshida ; Akari Suzuki ; Toru Motozaki ; Ikuko Kozawa ; Takashi Hayamizu ; Ryosuke Munakata ; Ken-ichi Takao ; Kin-ichi Tadano
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 3, 2007
• 年：2007
• 卷：72
• 期：16
• 页码：6143 - 6148
• 全文大小：211K
• 年卷期：v.72,no.16(August 3, 2007)
• ISSN：1520-6904

文摘

Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B,(+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations ofthe three tubelactomicins, for which planar structures had solely been reported. The total synthesis of(+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reactionfor constructing the highly functionalized octahydronaphthalene substructures.