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Total Synthesis of Lamellarins D, H, and R and Ningalin B Lamellarin类海洋天然产物的全合成 Liu,W;Jiang,H;Huang,L.Org.Lett.2010,12,312-315. 摘要：我们分别以Lamellarin D （7步）、H（7步）、R（5步）和B（5步）以相应的醛和胺为原料，利用醋酸银促进的多取代吡咯合成为关键反应完成海洋天然产物Lamellarin D、H和ningalin B的合成，该合成主要包括三个氧化偶联反应，一是AgOAc促进的1,3,4-三取代吡咯的合成，二是Pb(OAc)4介导的氧化内酯化反应和Kita’s(三氟醋酸碘苯氧化)氧化芳基-吡咯C-C键的形成。 A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving and AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)4-induced oxidative cyclization to form the lactone, and Kita’s oxidation reaction to form the pyrrole-arene C-C bond. 研究过程及实验：在1985年Faulkner和他的同事们第一次从Lamellarin A-D（Figure 1）（海生生物体和原核生物体等）分离出已经超过70多种lamellarin及相关吡咯生物碱被分离和结构鉴定，它们不但有着新颖的骨架，同时还显示着良好的生物活性，比如：细胞毒性，抗肿瘤活性，逆转多药耐药，HIV-1整合酶抑制活性生素活性，抗氧化活性等。近年来，lamellarin类生物碱的生物活性与构效关系的研究主要集中在抗肿瘤与抗HIV病毒方面。抗肿瘤活性：Lamellarin类生物碱对肿瘤细胞的抑制增殖作用。分别由于这一系列化合物新颖独特的化学结构、良好的生理活性和天然资源含量的稀少性，很快引起了包括Steglich,FaulknerIwao,Boger,Ruchirawat,Gupton,Handy,andAlvarez等一些有机合成化学家物学家的兴趣，分别采用不同的策略（如：仿生合成法、N-叶立德法、Michae加成法、Diels-Alder反应和缩环合成法、金属催化的交叉偶联反应等）对这类化进行化学全合成的研究，到目前为止已有多篇相关分子合成的报道。 Since the first isolation of lamellarins A-D (Figure 1) by Faulkner and co-workers in 1985,1 more than 70 different lamellarins and related naturally occurring pyrrole-derived alkaloids have been isolated from diverse marine organisms such as mollusks, ascidians, and sponges. The lamellarins and related pyrrole-derived alkaloids have shown promising biological activities such as antitumor activity, reversal of multidrug resistance (MDR), and HIV-1 integrase inhibition activity.2 In light of their fascinating novel structures,intriguing biological properties, and the difficulty in obtaininglarge quantities from natural sources, the lamellarins and relat