Convergent syntheses of polycyclic ethers. Illustrations of the utility of acetal-linked intermediates.
One of the most characteristic and spectacular class of compounds isolated from marine sources is the polycyclic ethers. Following the initial report of the structural determination of brevetoxin B, a variety of novel polycyclic ethers have begun to surface. These natural products include ciguatoxins, gambierol, gambieric acids, yessotoxins and gymnocins, each of which exhibit distinct biological properties such as cytotoxicity and neurotoxicity, as well as antiviral and antifungal activities. Because of these intriguing biological activities and their complex molecular architecture, the total synthesis of these compounds has been pursued by many laboratories over two decades. In particular, the development of novel convergent strategies to assemble the structural fragments is crucial for the successful construction of these nano-scale molecules. This Perspective will focus on a recent convergent methodology using an acetal-linkage as a key motif. Application of this methodology culminated in the total syntheses of gambierol and ciguatoxin CTX3C.
Inoue
Masayuki
M
Department of Chemistry, and Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. inoue@ykbsc.chem.tohoku.ac.jp
D000080:Acetals / Q000737:chemistry*; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D017971:Tin Compounds / Q000737:chemistry
D000080:Acetals; D004987:Ethers; D005609:Free Radicals; D012821:Silanes; D017971:Tin Compounds; C031525:stannane