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    188宝金博页面版: Two novel aconane-type diterpenes derived from C-nor-C19-diterpenoid alkaloid

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    内容提示： Two novel aconane-type diterpenes derived fromC-nor-C19-diterpenoid alkaloidXiang Li Shena,b, Qiao Hong Chena,Dong Lin Chena, Feng Peng Wanga,*aDepartment ofChemistry ofMedicinal Natural Products, West China College ofPharmacy,Sichuan University, Chengdu 610041, ChinabSecond Hospital ofSichuan University, Chengdu 610041, ChinaReceived 13 October 2008AbstractTwo novel C-nor-B-homo aconane-type diterpenes 4 and 5, featuring a unique eight-membered ring system, were obtained bythe treatment of C-nor-C19-diter...

    文档格式：PDF | 页数：4 | 浏览次数：73 | 上传日期：2015-04-06 12:35:50 | 文档星级：
    Two novel aconane-type diterpenes derived fromC-nor-C19-diterpenoid alkaloidXiang Li Shena,b, Qiao Hong Chena,Dong Lin Chena, Feng Peng Wanga,*aDepartment ofChemistry ofMedicinal Natural Products, West China College ofPharmacy,Sichuan University, Chengdu 610041, ChinabSecond Hospital ofSichuan University, Chengdu 610041, ChinaReceived 13 October 2008AbstractTwo novel C-nor-B-homo aconane-type diterpenes 4 and 5, featuring a unique eight-membered ring system, were obtained bythe treatment of C-nor-C19-diterpenoid alkaloid 3 with HNO2 in 8% and 21% yields, respectively. Structures of thesetwo compounds were established based on the combination of spectroscopic data, including HRESIMS, 1D and 2D NMR data.A plausible mechanism for the formation of 4 and 5 is also presented.# 2008 Feng Peng Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.Keywords: C19-diterpenoid alkaloid; C-nor-B-homo-aconane; Rearrangement; ImineThe diterpenoid alkaloids, displaying various interesting chemical reactions [1] and biological activities [2], are agroup ofcomplex natural products mainly from Aconitum and Delphinium plants [3]. Considering rich natural sourcesofsome C19-diterpenoid alkaloids such as yunaconitine and deltaline, we have attempted to seek an approach towardthe chemical conversion of C19-diterpenoid alkaloids to taxoids [4]. After a decade-long study on this researchprogram since 1994, we have finally achieved a novel approach to the taxane ABC ring system through chemicalconversion from C19-diterpenoid alkaloid deltaline [5]. Importantly, our journey along this chemical conversion led tothe discovery of numerous of intriguing reactions of C19-diterpenoid alkaloids [6–13]. Among these chemicalinvestigations, it is worthwhile to note that the N-atom-involving chemical reactions are very complicated. It wasreported that the denitrogenation of immonium salt 1 with NaNO2–NaOAc–HOAc could provide hemiacetal 2(Scheme 1) [14]. Based on this denitrogenation of the diterpenoid alkaloid, we initially attempted to prepare anaconane-type diterpene 6 employing the C-nor- C19-diterpenoid alkaloid 3 as a starting material. Surprisingly, twoC-nor-B-homo aconane-type diterpenes 4 and5 (instead ofthe ketal 6), characteristic ofaunique eight-membered ringsystem, were obtainedfrom the reaction ofC-nor-C19-diterpenoid alkaloid 3 with NaNO2/HOAc (Scheme 2). We wishto report herein this interesting reaction, along with the structural elucidation of these two novel C-nor-B-homowww.elsevier.com/locate/ccletAvailable online at www.sciencedirect.comChinese Chemical Letters 20 (2009) 431–434* Corresponding author.E-mail address: wfp@scu.edu.cn (F.P. Wang).1001-8417/$ –see front matter # 2008 Feng Peng Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.doi:10.1016/j.cclet.2008.12.028

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