Synthesis and Molecular Recognition of Biologically Active Marine Natural Products

近年来，人们发现了许多具有新颖结构和生物功能的有趣的海洋天然产物，通常数量很少。1)吡咯喹啉生物碱的合成研究一类新的吡咯喹啉生物碱是新西兰海绵、冲绳海绵和斐济海绵的代谢物。它们具有显著的抗肿瘤活性，特别是对拓扑异构酶II具有很强的抑制活性。我们成功地合成了去甲草素C、巴曲菌素C、异胡萝卜素C、马卡路菌素A、B、C和D。一些合成的中间体也被证明具有抗肿瘤活性。我们开发了新的合成方法学来构建…3)苔藓他汀类化合物的合成研究。Bryosteins是一类具有抗肿瘤活性的高含氧量的海洋天然产物。我们在克级合成Bryostatin 11方面做了大量的工作。此外，我们还可以合成两个主要的结构单元，它们包含了Bryostatin 11的所有碳原子。对该大环内酯的进一步合成研究正在进行中。4)从海绵和海鱼中产生的生物活性物质的合成研究我们已经合成了巴士丁、海藻硫蛋白和相关的海洋天然产物，它们都具有有趣的螺异恶唑环，并显示出抗菌活性。我们进一步尝试合成已分离出来的海兔代谢物沙棘溶素。我们还开发了一种新的合成方法，利用电化学技术来构建反式氢化天青烯，并由此衍生出一系列海洋天然产物。较少

Recently, a number of interesiting marine natural products with novel structures and biological functions have been found, usually in very small quantities. Accordingly, our great efforts have been focused on total syntheses of these compounds in gram scale, as follows.1)Synthetic studies on pyrroloquinoline alkaloidsA new class of pyrroloquinoline alkaloids have been isolated as metabolites of the New Zealand, Okinawan and Fijian sponges. They show remarkable antitumor activities and particularly possess potent inhibitory activities against the function of topoisomerase II.We successfully synthesized discorhabdin C, batzelline C, isobatzelline C, makaluvamines A, B, C and D.Some of their synthetic intermediates were also proved to have antitumor activities.2)Synthetic studies on novel pyrone-metabolites of some marine organismsPeroniatriols and ilikonapyrone are considered to be defensive substances of some kinds of marine molluscs. We developed new systhetic methodology to construct … More a fully substituted gamma-pyrone ring, and determined the absolute configurations of these pyrones by means of the above mentioned method.3)Synthetic studies on bryostatinsBryostatins, the highly oxygenated macrolides are one of the most attractive marine natural products for their therapeutically antineoplastic activities. Our considerable efforts have been made for syntheses of bryostatin 11 in gram scale. And we could synthesize two main moieties which include all of carbon atoms of bryostatin 11. Further synthetic study on this macrolide is in progress.4)Synthetic studies on bioactive substances produced by marine sponges and sea hearsWe had already synthesized bastadins, aerothionin and related marine natural products, all of which have an interesting spiroisoxazol ring and show antibacterial activities. We further attempt to synthesize psammaplysin which has been isolated as the metabolite of sea hare. We also developed a new synthetic method to construct trans-hydroazulenes, using electrochemical technique, from which a number of marine natural products will be derived. Less