A total synthesis of (−)-hortonone C

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• 作者：Doleshwar Niroula^a ; Liam P. Hallada^a ; ^b ; Snezna Rogelj^b ; Rodolfo Tello-Aburto^a ; ^{rodolfo.tello-aburto@nmt.edu}
• 关键词：Hortonones ; Natural products ; Total synthesis ; Asymmetric conjugate addition ; Hydroazulene ; Hydroindane
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：26 January 2017
• 年：2017
• 卷：73
• 期：4
• 页码：359-364
• 全文大小：420 K
• 卷排序：73

文摘

A total synthesis of the cytotoxic terpenoid hortonone C was accomplished and its absolute stereochemistry confirmed. Intermediate (+)-4 was synthesized using either an asymmetric conjugate addition strategy, or by elaboration of the Hajos-Parrish ketone. Reduction of (+)-4 under dissolving-metal conditions and trapping the enolate intermediate served to control the cis-stereochemistry at the ring fusion and provide a silyl enol ether necessary for ring expansion. Comparison of optical rotation data confirmed that the absolute configuration of natural hortonone C is (6S,7S,10S).