A modular synthesis of lamellarins has been developed. The key reactions in this synthesis are the assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones from a preexisting [1]benzopyrano[3,4-b]pyrrol4(3H)-one core and the appropriate arylboronic acids. The obtained 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones could be easily converted into the corresponding lamellarin derivatives by intramolecular annulation between the pyrrole nitrogen and the C2 aromatic ring. INTRODUCTION Lamellarins are polycyclic pyrrole alkaloids possessing a unique 14-phenyl-6H-[1]benzopyrano[4 ́,3 ́:4,5]pyrrolo[2,1-a]isoquinolin-6-one ring system. In rare cases (lamellarins O, P, Q, and R), the compounds possess simple, nonfused 3,4-diarylpyrrole-2-carboxylate structures. Since the first isolation of lamellarins A–D from the marine prosobranch mollusk Lamellaria sp. in 1985, more than 50 lamellarins have been isolated from tunicates, sponges, and prosobranchs. These lamellarins exhibit a wide range of useful biological activities: potent antiproliferative activity against several cancer cell lines, multi-drug resistance (MDR) reversal activity, anti-HIV activity, topoisomerase I inhibition, inhibition of mitochondrial function, and protein kinase inhibition. Because of their unique structures and significant biological activities, lamellarins have attracted the attention of synthetic organic and medicinal chemists. Since the first synthesis of lamellarins in 1997, numerous methods for their preparation have been proposed. The methods can be categorized into two groups: one utilizes formation of the pyrrole core as the key step and the other employs regioselective functionalization of the This paper is dedicated to Professor Dr. Masakatsu Shibasaki on the occasion of his 70th birthday. 950 HETEROCYCLES, Vol. 95, No. 2, 2017

中文翻译：

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1,2-二芳基化[1]苯并吡喃[3,4-b]pyrrol-4(3H)-one核的区域选择性组装合成层状蛋白

已经开发了层状蛋白的模块化合成。该合成中的关键反应是由预先存在的[1]苯并吡喃[3,4-b]吡咯4( 3H)-一个核心和适当的芳基硼酸。得到的1,2-二芳基[1]苯并吡喃[3,4-b]pyrrol-4(3H)-ones可以通过吡咯氮和C2芳环之间的分子内环化很容易地转化为相应的层状结构衍生物。引言 层层素是一种多环吡咯生物碱，具有独特的 14-苯基-6H-[1]苯并吡喃[4́,3́:4,5]吡咯并[2,1-a]异喹啉-6-环系统。在极少数情况下（层状蛋白 O、P、Q 和 R），这些化合物具有简单的非稠合 3,4-diarylpyrrole-2-carboxylate 结构。自从第一次从海洋前支软体动物 Lamellaria sp. 中分离出层状蛋白 A-D。1985 年，从被囊类动物、海绵类和前枝类动物中分离出 50 多种层状蛋白。这些层状蛋白表现出广泛的有用生物活性：针对几种癌细胞系的有效抗增殖活性、多药耐药性 (MDR) 逆转活性、抗 HIV 活性、拓扑异构酶 I 抑制、线粒体功能抑制和蛋白激酶抑制。由于其独特的结构和显着的生物活性，层状蛋白引起了合成有机化学家和药物化学家的关注。自 1997 年首次合成层状蛋白以来，已经提出了许多制备它们的方法。这些方法可以分为两组：一个利用吡咯核心的形成作为关键步骤，另一个利用区域选择性功能化。这篇论文献给Masakatsu Shibasaki教授70岁生日。950 杂环，卷。2017年95期第2期